Name: 10210-17-0|3-(4-Hydroxyphenyl)-1-propanol|95%
Brand: Ambeed
SKU: A174374
Price: 5.0 USD
Availability: InStock
Rating: 97 (35 reviews)

1
[ 54965-55-8 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
95.5%	With lithium borohydride In tetrahydrofuran at 70℃; for 22h;
	With lithium aluminium tetrahydride; diethyl ether

Reference： [1]Ohkata, Katsuo; Tamura, Yukiko; Shetuni, Brandon B.; Takagi, Ryukichi; Miyanaga, Wataru; Kojima, Satoshi; Paquette, Leo A. [Journal of the American Chemical Society, 2004, vol. 126, # 51, p. 16783 - 16792]
[2]Pearl [Journal of Organic Chemistry, 1959, vol. 24, p. 736,738]

2
[ 60-82-2 ]
[ 10210-17-0 ]
[ 501-97-3 ]
[ 108-46-3 ]

Reference： [1]Agricultural and Biological Chemistry,1989,vol. 53,p. 3087 - 3090

3
[ 25823-43-2 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With aluminum oxide In neat (no solvent) at 65℃; for 0.0416667h; microwave irradiation;

Reference： [1]Varma, Rajender S.; Varma, Manju; Chatterjee, Arnab K. [Journal of the Chemical Society. Perkin transactions I, 1993, # 9, p. 999 - 1000]

4
[ 61440-45-7 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogen In acetic acid
84.3%	With hydrogen In ethanol at 20℃;
0.149 g	With hydrogen In ethanol Ambient temperature;

Reference： [1]Henley-Smith, Peter; Whiting, Donald A.; Wood, Andrew F. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 614 - 622]
[2]Louis, Simon N.; Nero, Tracy L.; Iakovidis, Dimitri; Colagrande, Felicia M.; Jackman, Graham P.; Louis, William J. [European Journal of Medicinal Chemistry, 1999, vol. 34, # 11, p. 919 - 937]
[3]Ishii, Hisashi; Ishikawa, Tsutomu; Tohojoh, Toshiaki; Murakami, Keiko; Kawanable, Eri; et al. [Journal of the Chemical Society. Perkin transactions I, 1982, # 9, p. 2051 - 2058]

5
[ 10210-17-0 ]
[ 67856-28-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With pyridine; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature;
40%	With [bis(acetoxy)iodo]benzene In 2,2,2-trifluoroethanol at 20℃; for 16h;
39%	With [bis(acetoxy)iodo]benzene In ethyl acetate at 21℃; for 0.5h;

	Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 16 h / 0 - 20 °C / Reflux 2: 5,15,10,20-tetraphenylporphyrin; oxygen / chloroform / 48 h / 20 °C / Irradiation 3: triethylamine / chloroform / 2 h / 20 °C
	With 1,1,1,3',3',3'-hexafluoro-propanol; [bis(acetoxy)iodo]benzene In dichloromethane at 0℃; for 0.0833333h;

Reference： [1]Tamura, Yasumitsu; Yakura, Takayuki; Haruta, Jun-ichi; Kita, Yasuyuki [Journal of Organic Chemistry, 1987, vol. 52, # 17, p. 3927 - 3930]
[2]Ohkata, Katsuo; Tamura, Yukiko; Shetuni, Brandon B.; Takagi, Ryukichi; Miyanaga, Wataru; Kojima, Satoshi; Paquette, Leo A. [Journal of the American Chemical Society, 2004, vol. 126, # 51, p. 16783 - 16792]
[3]Wipf, Peter; Kim, Yuntae [Journal of the American Chemical Society, 1994, vol. 116, # 26, p. 11678 - 11688]
[4]Jones, Kevin M.; Hillringhaus, Tim; Klussmann, Martin [Tetrahedron Letters, 2013, vol. 54, # 25, p. 3294 - 3297]
[5]Canesi, Sylvain; Mammasse, Zahra; Signo, Kouassi [Journal of Organic Chemistry, 2020, vol. 85, # 4, p. 2832 - 2837]

6
[ 10210-17-0 ]
[ 52273-55-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen bromide at 80℃; for 20h;	15.1 Preparation of 4-(3-bromopropyl)phenol 48 wt% hydrogen bromide and 3- (4-hydroxyphenyl) -1-propanol(1.0 g, 6.57 mmol) was stirred at 80 ° C for 20 hours, and then cooled at room temperature. The reaction mixture was diluted in water and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. The residue was purified by column chromatography using hexane:The residue was purified by silica gel flash column chromatography using ethyl acetate as a mobile phase to give the desired product, 4- (3-bromopropyl) phenol(0.1.35 g, 96% yield)As a beige solid.
95%	With carbon tetrabromide; triphenylphosphine In dichloromethane Cooling with ice;
92%	With hydrogen bromide In water at 80℃; for 20h;	6 A mixture of 4-(3-hydroxy-propyl)-phenol (52.7 g, 346.3 mmol) in 48 wt % HBr (265 mL) was stirred at 80° C. for 20 h and then cooled to room temperature. Water (400 mL) was added, and the product was extracted with CH2Cl2 (500 mL). The extract was dried (MgSO4) and concentrated under reduced pressure to give the desired product as a beige solid (69 g, 92% yield). TLC (SiO2, CH2Cl2): Rf=0.37. 1H NMR (400 MHz, DMSO-d6): 9.18 (s, 1H), 6.99 (d, J=8.3, 2H), 6.67 (d, J=8.4, 2H), 3.47 (t, J=6.6, 2H), 2.58 (t, J=7.2, 2H), 2.05-1.95 (m, 2H).

92%	With hydrogen bromide In water at 80℃; for 20h;	6 EXAMPLE 6; 4- (3-BROMO-PROPYL)-PHENOL; A mixture OF 4- (3-HYDROXY-PROPYL)-PHENOL (52.7 g, 346.3 MMOL) in 48 wt % HBr (265 ML) WAS STIRRED AT 80 °C FOR 20 H AND THEN COOLED TO ROOM TEMPERATURE. P WATER (400 ML) WAS ADDED, AND THE PRODUCT WAS EXTRACTED WITH CH2CI2 (500 mL). The extract was dried (MGS04) and concentrated under reduced pressure to give the desired product as a beige solid (69 g, 92% yield). TLC (SIO2, CH2CI2) : Rf-0.37. 1H NMR (400 MHz, DMSO-d6) : 9.18 (s, 1H), 6.99 (d, J = 8.3, 2H), 6.67 (d, J = 8.4, 2H), 3.47 (t, J = 6.6, 2H), 2.58 (t, J = 7.2, 2H), 2.05-1. 95 (m, 2H)
92%	With hydrogen bromide In water at 80℃; for 20h;	6 Example 6 4-(3-bromo-propyl)-phenol A mixture of 4-(3-hydroxy-propyl)-phenol (52.7 9, 346.3 mmol) in 48 wt % HBr (265 mL) was stirred at 80° C. for 20 h and then cooled to rt. Water (400 mL) was added, and the product was extracted with CH2Cl2 (500 mL). The extract was dried (MgSO4) and concentrated to give the desired product as a beige solid (69 g, 92%). TLC (SiO2, CH2Cl2): Rf=0.37. 1H NMR (400 MHz, DMSO-d6): 9.18 (s, 1H), 6.99 (d, J=8.3, 2H), 6.67 (d, J=8.4, 2H), 3.47 (t, J=6.6, 2H), 2.58 (t, J=7.2, 2H), 2.05-1.95 (m, 2H).
91%	With carbon tetrabromide; N,N-dimethyl-formamide; sodium bromide; 4,7-diphenyl-2,1,3-benzothiadiazole In N,N-dimethyl-formamide at 20℃; for 24h; Schlenk technique; Irradiation; Green chemistry;
90%	With carbon tetrabromide In dichloromethane at -18 - 20℃; for 4h; Inert atmosphere;
84%	With carbon tetrabromide; tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate; N,N-dimethyl-formamide; sodium bromide at 25 - 30℃; Inert atmosphere; visible-light irradiation;
75%	With sulfuric acid; hydrogen bromide for 6h; Heating;
69%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃;	4-(3-bromopropyl)phenol(10a) 4-(3-Hydroxypropyl)phenol(0.68 g, 4.47 mmol) was dissolved in dry DCM (45 mL). After theaddition of CBr4(3.0 g, 9.05 mmol), the solution was cooled to 0°C for theportion-wise addition of PPh3(2.9 g, 11.05 mmol). The solution was allowed to warm to roomtemperature overnight and the solvent was removed invacuo.The crude product was purified by flash column chromatography elutingwith EtOAc/hexanes (20:80) to obtain 4-(3-bromopropyl)phenol as ayellow oil (0.67 g, 3.11 mmol, 69%). 1HNMR: (500 MHz, CDCl3):δ 7.07-7.05 (d, J= 8.0 Hz,2H), 6.77-6.75 (d, J= 8.5 Hz,2H), 3.39-3.36 (t, J= 7.0 Hz,2H), 2.72-2.69 (t, J= 7.0 Hz,2H), 2.14-2.09 (p, J= 6.5,2H); 13CNMR: (125 MHz, CDCl3)δ: 153.9, 132.8, 129.8, 115.4, 34.4, 33.2, 33.1.
53%	With phosphorus tribromide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	Preparation of 1k ^[2] A solution of compound 62 (9.0 g, 50 mmol) in anhydrous THF (100 ml) was slowly added to a well stirred suspension of LiAlH4 (3 g, 79 mmol, 1.6 equiv.) in anhydrous THF (300 ml) at 0 °C under argon atmosphere. The mixture was allowed to reach room temperature and then stirred for 2 hours. Then water (3 ml), 15% NaOH aqueous (3 ml) and water (3 ml) were added sequentially. Then the mixture was filtered, washed with EtOAc (100 ml), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified flash silica gel (300-400 mesh) chromatography to afford 63 as a white solid (2.45 g, 32% yield). To a well-stirred solution of 63 (2.45 g, 16.1 mmol) in anhydrous DCM (300 ml) was added PBr3 (2.25 ml, 19 mmol, 1.2 equiv.) dropwise at 0 °C under argon atmosphere, then stirred for 1 hour, then allowed tostirred in room temperature for 5 hours. The resulting mixture was washed with water (50 ml×2) and saturated aqueous of NaHCO3 (100 ml), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified flash silica gel (300-400 mesh) chromatography to afford 64 as a yellow oil (1.7 g, 53% yield). A well stirred solution of compound 64 (1.7 g, 7.9 mmol) in 5 ml of propargyl alcohol was cooled to 0 °C and treated with phenyliodine(III) diacetate (PIDA, 3.0 g, 12 mmol, 1.5 equiv.) in several portions. The resulting mixture was warmed to room temperature and stirred overnight. Then the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL × 3). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography using hexane / ethyl acetate eluent to afford the desired product 1k (600 mg, 39.7% yield) as a yellow oil.
	With hydrogen bromide In water	26 Preparation of 4-(3-bromopropyl)phenol EXAMPLE 26 Preparation of 4-(3-bromopropyl)phenol To 48% hydrobromic acid solution (110 g) was added 4-(3-hydroxypropyl)phenol (25 g) and heated on a steam bath for 3 hours. After cooling, water (500 ml) was added, the oil was extracted with ether, washed with water and then with dilute sodium bicarbonate solution. The etheral extract was dried over potassium carbonate, evaporated and the residue was distilled in a Kugelrohr apparatus giving 29.6 g (84%) of 4-(3-bromopropyl)phenol, bp 180° (2 mm). The product was 92.6% pure by gas chromatography and mass spectrum was compatible with 4-(3-bromopropyl)phenol.
	With sulfuric acid; hydrogen bromide In water for 6h; Reflux;	A solution of 3-(4-hydroxyphenyl)-1-propanol (2.50 g, 16.5 mmol), sulfuric acid (1 ml) and aqueous hydrobromic acid (48%, 15 ml) was heated at reflux for 6 h, After cooling to rt, the reaction mixture was neutralised with saturated sodium hydrogencarbonate solution, and then washed with ethyl acetate (3×60 ml). The combined organic layers were washed with brine (100 ml), dried over magnesium sulfate, and then concentrated in vacuo. Purification by flash chromatography on silica (dichloromethane) afforded the titled compound as a pale yellow solid (2.70 g, 78%).1H NMR (300 MHz; CDCl3) 2.15 (2H, tt, J 6.6, 6.6 Hz), 2.78 (2H, t, J 6.6 Hz), 3.38 (2H, t, J 6.6 Hz), 6.79 (2H, d, J 9.0 Hz, Ph-H), 7.06 (2H, d, J 9.0 Hz, Ph-H);13C NMR (75.5 MHz; CDCl3) 33.0, 33.2 and 34.4, 115.3, 129.7, 132.8, 153.8.m/z (-ES) 215 (100, [M-H]-).
	With phosphorus tribromide In dichloromethane at 0℃; for 1h; Inert atmosphere;	2 To a solution of Compound 2 (10 g, 65.7 mmol) in dry DCM (100 mL) was added PBr3 (21.4 g, 78.8 mmol) dropwise at 0° C. under nitrogen. The resulting mixture was stirred for 1 hour then washed with water (2×100 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to yield crude compound 1 as a yellow oil (7.8 g). A portion of the crude material (6.8 g) was purified by column chromatography (hexanes:EtOAc 10:1) to yield Compound 3 as a colorless oil (5 g.). To a solution of Compound 3 (3 g, 13.9 mmol) in MeCN (30 mL) was added AgNO3 (2.8 g, 16.7 mmol). The resulting mixture was stirred at 0° C. for 5 hours (dark) under nitrogen. After cooling, the mixture was filtered and diluted with EtOAc (30 mL). The organic layer was washed with water and saturated aqueous NaCl, dried, and evaporated. The remaining residue was purified by column chromatography (hexanes:EtOAc 15:1) to yield the title compound as a yellow oil (1.7 g).

Reference： [1]Current Patent Assignee: SEOUL NATIONAL UNIVERSITY - KR2016/135880, 2016, A Location in patent: Paragraph 0236-0239
[2]Location in patent: experimental part Chang, Ching-Yao [Journal of the Chinese Chemical Society, 2011, vol. 58, # 3, p. 286 - 289]
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - US2008/194630, 2008, A1 Location in patent: Page/Page column 29
[4]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2005/12296, 2005, A1 Location in patent: Page/Page column 78
[5]Current Patent Assignee: JOHNSON & JOHNSON INC - US2006/223792, 2006, A1 Location in patent: Page/Page column 23
[6]Li, Run; Gehrig, Dominik W.; Ramanan, Charusheela; Blom, Paul W. M.; Kohl, Fabien F.; Wagner, Manfred; Landfester, Katharina; Zhang, Kai A. I. [Advanced Synthesis and Catalysis, 2019, vol. 361, # 16, p. 3852 - 3859]
[7]Romussi, Alessia; Cappa, Anna; Vianello, Paola; Brambillasca, Silvia; Cera, Maria Rosaria; Dal Zuffo, Roberto; Fagà, Giovanni; Fattori, Raimondo; Moretti, Loris; Trifirò, Paolo; Villa, Manuela; Vultaggio, Stefania; Cecatiello, Valentina; Pasqualato, Sebastiano; Dondio, Giulio; So, Chi Wai Eric; Minucci, Saverio; Sartori, Luca; Varasi, Mario; Mercurio, Ciro [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 5, p. 754 - 759]
[8]Location in patent: experimental part Dai, Chunhui; Narayanam, Jagan M.R.; Stephenson, Corey R.J. [Nature Chemistry, 2011, vol. 3, # 2, p. 140 - 145]
[9]Bell, Vivien L.; Giddings, Peter J.; Holmes, Andrew B.; Mock, Graham A.; Raphael, Ralph A. [Journal of the Chemical Society. Perkin transactions I, 1986, p. 1515 - 1522]
[10]McLane, Richard D.; Le Cozannet-Laidin, Léon; Boyle, Maxwell S.; Lanzillotta, Lindsey; Taylor, Zachary L.; Anthony, Sarah R.; Tranter, Michael; Onorato, Amber J. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 3, p. 334 - 338]
[11]He, Cheng-Yu; Xie, Li-Bo; Ding, Rui; Tian, Ping; Lin, Guo-Qiang [Tetrahedron, 2019, vol. 75, # 12, p. 1682 - 1688]
[12]Current Patent Assignee: ROCHE HOLDING AG - US4471116, 1984, A
[13]Current Patent Assignee: IP21PO INNOVATIONS LIMITED - US2009/221702, 2009, A1 Location in patent: Page/Page column 10-11
[14]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - US2013/323271, 2013, A1 Location in patent: Paragraph 0389

7
[ 5597-50-2 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 3-(4-hydroxyphenyl)propionic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 - 5h; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran; ethyl acetate	1.i Step (i); To a suspension of LAH (22.1 g, 2.5 eq, 583 mmol) in dry THF (1.0 L),was added dropwise a THF (50 mL) solution of methyl 3-(4-hydroxyphenyl)propionate(21 g, 1.0 eq, 116 mmol) at RT. The reaction mixture was refluxed for 4-5 h. It wasworked up by quenching with excess ethyl acetate followed by addition of water (23mL), 15% aq. NaOH (23 mL) and water (70 mL) under controlled stirring andmaintaining RT. To the workup mixture cone. HC1 was added to adjust the pH at 7.0. Itwas then filtered through celite and washed with ethyl acetate. Combined filtrate wasdried QS^SO/t) and condensed. Obtained residue was chromatographed (ethylacetate/hexanes) to obtain 3-(4-hydroxyphenyl)propanol (17 g, 100%) as white solid.Mp: 52-54°C.'H NMR (CDC13, 200 MHz 5: 1.78-1.86 (m, 2H); 2.63 (t, J = 7.9 Hz,2H); 3.67 (t, J = 6.3 Hz, 2H); 6.74 (d, J = 8.8 Hz, 2H); 7.05 (d, J = 8.8 Hz, 2H).IR (neat) cm-1: 3485, 3029, 2940, 1505.Massm/z(CI):
100%	Stage #1: 3-(4-hydroxyphenyl)propionic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 - 5h; Heating / reflux; Stage #2: With sodium hydroxide In tetrahydrofuran; water; ethyl acetate at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate	1.i To a suspension of LAH (22.1 g, 2.5 eq, 583 mmol) in dry THF (1.0 L), was added dropwise a THF (50 mL) solution of methyl 3-(4-hydroxyphenyl)propionate (21 g, 1.0 eq, 116 mmol) at RT. The reaction mixture was refluxed for 4-5 h. It was worked up by quenching with excess ethyl acetate followed by addition of water (23 mL), 15% aq. NaOH (23 mL) and water (70 mL) under controlled stirring and maintaining RT. To the workup mixture conc. HCl was added to adjust the pH at 7.0. It was then filtered through celite and washed with ethyl acetate. Combined filtrate was dried (Na2SO4) and condensed. Obtained residue was chromatographed (ethyl acetate/hexanes) to obtain 3-(4-hydroxyphenyl)propanol (17 g, 100%) as white solid. Mp: 52-54° C. 1H NMR (CDCl3, 200 MHz δ: 1.78-1.86 (m, 2H); 2.63 (t, J=7.9 Hz, 2H); 3.67 (t, J=6.3 Hz, 2H); 6.74 (d, J=8.8 Hz, 2H); 7.05 (d, J=8.8 Hz, 2H). IR (neat) cm-1: 3485, 3029, 2940, 1505. Mass m/z (CI): 152 [M+1].
100%	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 - 5h; Heating / reflux;	i Step (i) To a suspension of LAH (22.1 g, 2.5 eq, 583 mmol) in dry THF (1.0 L), was added dropwise a THF (50 mL) solution of methyl 3-(4-hydroxyphenyl)propionate (21 g, 1.0 eq, 116 mmol) at RT. The reaction mixture was refluxed for 4-5 h. It was worked up by quenching with excess ethyl acetate followed by addition of water (23 mL), 15% aq. NaOH (23 mL) and water (70 mL) under controlled stirring and maintaining RT. To the workup mixture conc. HCl was added to adjust the pH at 7.0. It was then filtered through celite and washed with ethyl acetate. Combined filtrate was dried (Na2SO4) and condensed. Obtained residue was chromatographed (ethyl acetate/hexanes) to obtain 3-(4-hydroxyphenyl)propanol (17 g, 100%) as white solid. Mp: 52-54° C. [0183] 1H NMR (CDCl3, 200 MHz δ: 1.78-1.86 (m, 2H); 2.63 (t, J=7.9 Hz, 2H); 3.67 (t, J=6.3 Hz, 2H); 6.74 (d, J=8.8 Hz, 2H); 7.05 (d, J=8.8 Hz, 2H). IR (neat) cm-1: 3485, 3029, 2940, 1505. [0184] Mass m/z (CI): 152 [M+1].

84.2%	With sodium tetrahydroborate In methanol at 20℃; for 3h; Cooling with ice;	16.a (a) 4-(3-hydroxypropyl) phenol [0241] 45.0 g (0.25 mol) of methyl p-hydroxyphenylpropionate was dissolved in 200 mL of methanol, cooled in an ice bath. 14.2 g (0.375 mol) of sodium borohydride was added in batches, and the addition was completed within about 1 hour. The reaction was continued with stirring at room temperature for 2 hours. Thin layer detection showed that the raw materials was reacted completely. The solvent was removed under reduced pressure. The residue was dissolved in water which is adjusted to be with the pH 2 by adding 2M hydrochloric acid. The solution was extracted with dichloromethane three times (200 mL3). The extracts were combined, and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, the solvent was removed under reduced pressure, and the residue was crystallized with dichloromethane and petroleum ether (1/5). 32.0g of the target compound was obtained with a yield of 84.2%.
32%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	Preparation of 1k ^[2] A solution of compound 62 (9.0 g, 50 mmol) in anhydrous THF (100 ml) was slowly added to a well stirred suspension of LiAlH4 (3 g, 79 mmol, 1.6 equiv.) in anhydrous THF (300 ml) at 0 °C under argon atmosphere. The mixture was allowed to reach room temperature and then stirred for 2 hours. Then water (3 ml), 15% NaOH aqueous (3 ml) and water (3 ml) were added sequentially. Then the mixture was filtered, washed with EtOAc (100 ml), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified flash silica gel (300-400 mesh) chromatography to afford 63 as a white solid (2.45 g, 32% yield). To a well-stirred solution of 63 (2.45 g, 16.1 mmol) in anhydrous DCM (300 ml) was added PBr3 (2.25 ml, 19 mmol, 1.2 equiv.) dropwise at 0 °C under argon atmosphere, then stirred for 1 hour, then allowed tostirred in room temperature for 5 hours. The resulting mixture was washed with water (50 ml×2) and saturated aqueous of NaHCO3 (100 ml), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified flash silica gel (300-400 mesh) chromatography to afford 64 as a yellow oil (1.7 g, 53% yield). A well stirred solution of compound 64 (1.7 g, 7.9 mmol) in 5 ml of propargyl alcohol was cooled to 0 °C and treated with phenyliodine(III) diacetate (PIDA, 3.0 g, 12 mmol, 1.5 equiv.) in several portions. The resulting mixture was warmed to room temperature and stirred overnight. Then the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL × 3). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography using hexane / ethyl acetate eluent to afford the desired product 1k (600 mg, 39.7% yield) as a yellow oil.
	With lithium borohydride In diethyl ether; toluene for 0.25h; Heating;
10 g	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	2 To a solution of 3-(4-hydroxyphenyl)propionic acid (20 mg, 120 mmol) in MeOH (300 mL) was added SOCl2 (28.6 g, 240 mmol) at 0° C. under nitrogen. The resulting mixture was stirred overnight then concentrated in vacuo. The residue was dissolved in EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (2*50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to yield Compound 1 as a red oil (21.2 g). A solution of Compound 1 (19 g, 106 mmol) in dry THF (200 mL) was slowly added to a suspension of LAH (6 g, 158 mmol) in dry THF (200 mL) at 0° C. under nitrogen. The mixture was allowed to reach room temperature and was then stirred for 2 hours. Then water (6 mL) and 15% aqueous NaOH (24 mL) were added. Additional water (6 mL) was added to quench the reaction. The solids were filtered and the filter cake was washed with EtOAc several times. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (hexanes:EtOAc 8:1˜5:1˜2:1) to yield Compound 2 as a yellow oil (10 g).

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2006/1795, 2006, A1 Location in patent: Page/Page column 12
[2]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2005/277693, 2005, A1 Location in patent: Page/Page column 5
[3]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2003/229083, 2003, A1 Location in patent: Page 19-20
[4]Current Patent Assignee: BEIJING SHOWBY PHARMACEUTICAL - EP3556435, 2019, A1 Location in patent: Paragraph 0241
[5]He, Cheng-Yu; Xie, Li-Bo; Ding, Rui; Tian, Ping; Lin, Guo-Qiang [Tetrahedron, 2019, vol. 75, # 12, p. 1682 - 1688]
[6]Lam, Thi Bach Tuyet; Iiyama, Kenji; Stone, Bruce A. [Phytochemistry, 1992, vol. 31, # 4, p. 1179 - 1184]
[7]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - US2013/323271, 2013, A1 Location in patent: Paragraph 0387; 0388

8
[ 10210-17-0 ]
[ 100-44-7 ]
[ 61440-45-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In ethanol for 6h; Inert atmosphere; Reflux;	3-(4-benzyloxyphenyl)propan-1-ol 53 To a 50mL flame-dried round-bottom flask was added 3-(4-hydroxyphenyl)-propan-1-ol 52 (716 mg,4.70 mmol) and potassium carbonate (974 mg, 7.05 mmol). Absolute ethanol (10 mL, 200 Proof) wasadded to dissolve the aldehyde. Benzyl chloride (0.59 mL, 5.17 mmol) was added into the stirringsuspension before the round-bottom was connected with a jacketed condenser. The reaction mixturewas heated under nitrogen atmosphere and refluxed for 6 h. The white precipitate was filtered afterthe mixture was cooled down to room temperature. The filtrate was concentrated and purified by flashcolumn chromatography (4:1 hexanes/EtOAc) to afford alcohol 53 as a white solid (mp 63-64 °C) in95% yield (1.08 mg, 4.45 mmol). Spectral data for 53: 1H NMR (500 MHz, CDCl3) δ 1.26 (s, 1H), 1.87 (m, 2H), 2.66 (t, 2H, J = 7.5 Hz),3.67 (t, 2H, J = 6.8 Hz), 5.05 (s, 2H), 6.91 (d, 2H, J = 7.8 Hz), 7.12 (d, 2H, J = 7.8 Hz), 7.32 (m, 1H),7.38 (t, 2H, J = 7.8 Hz), 7.44 (d, 2H, J = 7.8 Hz); 13C NMR (125 MHz, CDCl3) δ 31.31, 34.56, 62.44,70.21, 114.94, 127.61, 128.04, 128.70, 129.47, 134.28, 137.33, 157.20; These spectral data matchwith those previously reported on this compound (Boll, P. M.; Hald, M.; Parmar, V. S.; Tyagi, O. D.;Bisht, K. S.; Sharma, N. K.; Hansen, S. Phytochemistry, 1992, 31, 1035).
94%	With potassium carbonate In ethanol for 3h; Heating;
	With sodium hydride 1.) DMF, 50 deg C 2.) 50 deg C; Yield given. Multistep reaction;

Reference： [1]Klucznik, Tomasz; Mikulak-Klucznik, Barbara; McCormack, Michael P.; Lima, Heather; Szymkuć, Sara; Bhowmick, Manishabrata; Molga, Karol; Zhou, Yubai; Rickershauser, Lindsey; Gajewska, Ewa P.; Toutchkine, Alexei; Dittwald, Piotr; Startek, Michał P.; Kirkovits, Gregory J.; Roszak, Rafał; Adamski, Ariel; Sieredzińska, Bianka; Mrksich, Milan; Trice, Sarah L.J.; Grzybowski, Bartosz A. [Chem, 2018, vol. 4, # 3, p. 522 - 532]
[2]Boll, Per M.; Hald, Mogens; Parmar, Virinder S.; Tyagi, Om Dutt; Bisht, Kirpal S.; et al. [Phytochemistry, 1992, vol. 31, # 3, p. 1035 - 1037]
[3]Ronald, Robert C.; Wheeler, Carl J. [Journal of Organic Chemistry, 1984, vol. 49, p. 1658 - 1660]

9
[ 10210-17-0 ]
[ 107-30-2 ]
[ 74882-15-8 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium hydride In N,N-dimethyl-formamide for 2h; Ambient temperature;
4.08 g	With potassium carbonate In acetone for 0.5h; Heating;
	With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Hori, Manabu; Janda, Kim D. [Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 889 - 894]
[2]Henley-Smith, Peter; Whiting, Donald A.; Wood, Andrew F. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 614 - 622]
[3]Fujioka, Hiromichi; Kubo, Ozora; Senami, Kento; Minamitsuji, Yutaka; Maegawa, Tomohiro [Chemical Communications, 2009, # 29, p. 4429 - 4431]

10
bis(t-butyldimethylsilyl)-3-(4-hydroxyphenyl)propanol [ No CAS ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	for 0.183333h; Irradiation;
75%	With cerium(IV) triflate In acetonitrile at 20℃; for 0.25h;

Reference： [1]Varma, Rajender S.; Lamture, Jagannath B.; Varma, Manju [Tetrahedron Letters, 1993, vol. 34, # 19, p. 3029 - 3032]
[2]Bartoli, Giuseppe; Cupone, Giovanna; Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Procopio, Antonio; Sambri, Letizia; Tagarelli, Antonio [Tetrahedron Letters, 2002, vol. 43, # 34, p. 5945 - 5947]

11
[ 10210-17-0 ]
[ 107-30-2 ]
3-(4-(Methoxymethoxy)phenyl)propyl methoxymethyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide 1.) r.t., 1.5 h, 2.) r.t., 20 h;
	With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	4.2.1. Preparation of 1a-d, 1k, 1o, and 1p^10b General procedure: A solution of an alcohol (1 equiv), MOMCl (1.5-1.8 equiv), iPr2NEt (3-3.6 equiv), and DMAP (0.1 equiv) in dry CH2Cl2 (0.2-0.5 M) was stirred at 0 °C to rt under N2. After disappearance of the alcohol on TLC, the mixture was evaporated in vacuo. The residue was purified by flash SiO2 column chromatography to give a MOM/ether. 1a,10b 1b,23 1c,24 1d,25 1o,26 and 1p27 are known compounds.

Reference： [1]Agharahimi, Mohamad R.; LeBel, Norman A. [Journal of Organic Chemistry, 1995, vol. 60, # 6, p. 1856 - 1863]
[2]Location in patent: experimental part Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro [Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960]

12
[ 2417-73-4 ]
[ 10210-17-0 ]
[ 135810-05-8 ]

Yield	Reaction Conditions	Operation in experiment
84.2%		a) [4- (3-HYDROXYPROPYL)] phenol (1.0 g, 6.57 mmol) and methyl [2- (BROMOMETHYL) BENZOATE] (1.66 g, 7.23 mmol) was dissolved in acetonitrile (10 [ML).] Potassium carbonate (1.82 g, 13.14 mmol) was added and the mixture was stirred at [60 C FOR] three hours. Polymersupported trisamine (0.3 eqv) was added and the solution was stirred at room temperature over night. The PS-trisamine was filtered of and the acetonitrile was removed by evaporation. EtOAc (10 [ML)] was added and the organic layer was washed with 3 portions of water (3 X 10 [ML).] The organic phase was dried [(MGS04)] and the solvent was removed by evaporation to give 1.66 gram of methyl 2-[4-(3-hydroxypropyl)phenoxy]- methyl} benzoate (yield 84.2%). [1HNMR] (500 MHz, CDC13) : 8 1.9 (m, 2H), 2.65 (t, 2H), 3.25 (s, 1H), 3.65 (t, 2H), 3.85 (s, 3H), 5.45 (s, 2H), 6.95 (d, [2H),] 7.15 (d, 2H), 7.35 (t, [1H),] 7.5 (t, 1H), 7.75 (d, 1H), 8.05 (d, 1H).
	With sodium hydroxide; potassium carbonate;potassium iodide; In hexane; dichloromethane; ethyl acetate; butanone;	EXAMPLE 17 2-[[4-(3-Hydroxypropyl)phenoxy]methyl]benzoic acid methyl ester A stirring degassed suspension of 57.9 g of 3-(4-hydroxyphenyl)propanol, 157 g of potassium carbonate, and a catalytic amount of potassium iodide in 500 ml of 2-butanone was treated dropwise over several minutes with a solution of 87.6 g of 2-(bromomethyl)benzoic acid methyl ester in 500 ml of 2-butanone. The resulting mixture was allowed to reflux for 24 hours and the resulting suspension was then stirred at room temperature for an additional 6 hours. The solids were removed by filtration and the product solution was concentrated to an oil in vacuo. The oil was partitioned against a total of 500 ml of methylene chloride and 1500 ml of 10% aqueous sodium hydroxide. The resulting pH of the final aqueous phase was above 12. The organic phase was washed with 500 ml of water, dried (Na2 SO4), and concentrated to an oil in vacuo. Thin layer analysis indicated a mixture which was separated via HPLC. Poor initial separation gave a mixture, which was separated using hexane in ethyl acetate as eluent to give 68.71 g of 2-[[4-(3-hydroxypropyl)phenoxy]methyl]benzoic acid methyl ester as an oil, which solidified to an amorphous material upon standing at room temperature, m.p. 50.5-52 C.

Reference： [1]Patent: WO2004/295,2003,A1 .Location in patent: Page 55-57, 59
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 246 - 252
[3]Patent: US5840749,1998,A

13
[ 501-97-3 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With borane-THF; Trimethyl borate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;	4-(3-hydroxypropyl)phenol(9a) 3-(4-Hydroxyphenyl)propionicacid (1.66 g, 10.0 mmol) was dissolved in dry THF (10 mL) under argonand trimethyl borate (3.35 mL, 30.0 mmol) was added. Separately,BH3.THFcomplex solution (20.0 mL, 20.0 mmol, 1.0 M solution in THF) wascooled to 0°C. The acid solution was added dropwise to theBH3.THFcomplex solution and the reaction mixture was stirred at 0°C for4 h. The reaction mixture was quenched with H2O(10 mL) and extracted with EtOAc (3 x 30 mL). The organic extractswere combined, dried over anhydrous MgSO4,filtered, and concentrated invacuoto obtain 4-(3-hydroxypropyl)phenol as a yellow oil (1.51 g, 9.9mmol, 99%) that was used without further purification. 1HNMR (500 MHz, CDCl3)δ 7.07-7.05 (d, J= 8.5 Hz,2H), 6.76-6.74 (d, J= 8.5 Hz,2H), 3.68-3.65 (t, J= 6.5 Hz,2H), 2.65-2.62 (t, J= 7.5 Hz,2H), 1.88-1.82 (p, J= 6.5 Hz,2H); 13CNMR: (125 MHz, CDCl3)δ 153.9, 133.8, 129.6, 115.3, 62.4, 34.4, 31.2.
98%	With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h;
98%	With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;	4.1 Preparation of trans-4-{3-[ethyl-(4-phenylcyclohexyl)amino]propyl}phenol EXAMPLE 4 [0184] Preparation of trans-4-{3-[ethyl-(4-phenylcyclohexyl)amino]propyl}phenol [CHEMMOL-00016] [0185] Step 1: To an ice-cold, stirred solution of 3-(4-hydroxyphenyl)propionic acid 7 (5.43 g, 32.7 mmol) in anhydrous THF (60 mL) was added BH3SMe2 (3.6 mL of a 1 M solution in THF, 3.6 mmol). The reaction was allowed to warm to room temperature overnight and then quenched with MeOH (100 mL). Concentration under reduced pressure gave alcohol 12 (4.96 g, 98%) as a white solid: 1H NMR (500 MHz, CDCl3) ? 7.04 (d, J=8 Hz, 2H), 6.75 (d, J=8 Hz, 2H), 3.67 (m, 2), 2.63 (t, J=7 Hz, 2H), 1.86 (m, 2H).

91%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
88%	With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 2h;
50.6%	With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Heating;
	Multi-step reaction with 2 steps 1: H₂SO₄ / 1.5 h / Heating 2: 13.5 g / LiAlH₄ / tetrahydrofuran / 12 h / 55 °C
	Multi-step reaction with 3 steps 1: 97.1 percent / NaOH / H₂O / 0 - 20 °C 2: 100 percent / K₂CO₃ / dimethylformamide / 23 h / 20 °C 3: 95.5 percent / LiBH₄ / tetrahydrofuran / 22 h / 70 °C

Reference： [1]McLane, Richard D.; Le Cozannet-Laidin, Léon; Boyle, Maxwell S.; Lanzillotta, Lindsey; Taylor, Zachary L.; Anthony, Sarah R.; Tranter, Michael; Onorato, Amber J. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 3, p. 334 - 338]
[2]Zhou, Yuhan; Gao, Guchao; Li, Hui; Qu, Jingping [Tetrahedron Letters, 2008, vol. 49, # 20, p. 3260 - 3263]
[3]Current Patent Assignee: PFIZER INC - US2003/225164, 2003, A1 Location in patent: Page 11-12
[4]Liang, Huan; Ciufolini, Marco A. [Chemistry - A European Journal, 2010, vol. 16, # 44, p. 13262 - 13270]
[5]Hori, Manabu; Janda, Kim D. [Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 889 - 894]
[6]González, Antonio G.; Silva, Margarita Hernández; Padrón, Juan I.; León, Francisco; Reyes, Eduardo; Álvarez-Mon, Melchor; Pivel, Juan P.; Quintana, José; Estévez, Francisco; Bermejo, Jaime [Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2358 - 2361]
[7]Ghirmai, Senait; Mume, Eskender; Lundqvist, Hans; Tolmachev, Vladimir; Sjoeberg, Stefan [Journal of labelled compounds and radiopharmaceuticals, 2005, vol. 48, # 12, p. 855 - 871]
[8]Ohkata, Katsuo; Tamura, Yukiko; Shetuni, Brandon B.; Takagi, Ryukichi; Miyanaga, Wataru; Kojima, Satoshi; Paquette, Leo A. [Journal of the American Chemical Society, 2004, vol. 126, # 51, p. 16783 - 16792]

14
[ 10210-17-0 ]
[ 100-39-0 ]
[ 61440-45-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In acetone at 20℃; for 12h;	3-(4-(Benzyloxy)phenyl)propanal (13) To a solution of 4-(3-hydroxypropyl)phenol (1.0 equiv.,1 mmol) in acetone (0.05 M) was added K2CO3 (1.5 equiv.,1.5 mmol), followed by the addition of benzyl bromide (1.2 equiv., 1.2 mmol) dropwise at rt, and the mixture was stirred at rt for 12 h. After completion, the solvent was removed under reduced pressure, and the residue was washed with H2O (30 mL) and extracted with ethyl acetate (320 mL); the organic layers were dried over MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography (hexane/ethyl acetate 10 : 1 → 5 : 1) to give the product 3-(4-(benzyloxy)phenyl)propan-1-ol as a white solid (230 mg, 95% yield). Rf (hexane/ethyl acetate 4 : 1) 0.30. δH (400 MHz, CDCl3) 7.48-7.33 (5H, m), 7.15 (2H, ddd, J 2.8, 5.2, 9.6), 6.95 (2H, ddd, J 2.8, 5.2, 9.6), 5.06 (2H, s), 3.66 (2H, t, J 6.4), 2.70-2.66 (2H, m), 2.19(1H, s), 1.92-1.85 (2H, m). δC (100 MHz, CDCl3) 157.1, 137.3, 134.3, 129.4, 128.6, 127.9, 127.5, 114.9, 70.1, 62.1, 34.4, 31.2. The spectroscopic data matched those reported in the literature.[16]
92%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;
90%	With sodium hydride In N,N-dimethyl-formamide for 12h; Heating;

90%	With potassium carbonate In acetone for 10h; Reflux; Inert atmosphere;	3-(4-Benzyloxy)phenylpropan-1-ol (3): To a stirred solution of 4-(3-hydroxypropyl)phenol (2) (2.0 g, 13.5 mmol) in acetone (50 mL), K2CO3 (3.6 g, 26.3 mmol), benzyl bromide (2.3 g, 13.5 mmol) were added sequentially and stirred under reflux conditions for 10 h. After completion of the reaction, the reaction was taken into CH2Cl2 (25 mL), washed with brine (1 × 10 mL), dried over anhydrous Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography using EtOAc-hexane (15:85) as eluant to give the required benzyl ether 3 as a solid (3.0 g, 90 %); m.p.: 54-56 °C; IR (KBr, νmax, cm-1): 3362, 2927, 2860, 1510, 1241; 1H NMR (200 MHz, CDCl3): δ 1.40 (bs, 1H), 1.76-1.94 (m, 2H), 2.66 (t, 2H, J = 6.9 Hz), 3.64 (t, 2H, J = 6.0 Hz), 5.04 (s, 2H), 6.86 (d, 2H, J = 8.6 Hz), 7.09 (d, 2H, J = 7.8 Hz), 7.20-7.50 (m,5H) ppm; 13C NMR (75 MHz, CDCl3): δ 31.2, 34.4, 62.2, 70.1, 114.9, 127.5, 127.9, 128.4, 129.4, 134.3, 137.3, 157.1 ppm; Mass (EI): 242 (M)+, 141, 91, 77, 65, 51.
80%	In dichloromethane at 0℃;
70%	With sodium hydride In N,N-dimethyl-formamide for 3h; from 0 deg C to RT;
62%	With potassium carbonate In acetone for 2h; Heating / reflux;	4.2 Preparation of trans-4-{3-[ethyl-(4-phenylcyclohexyl)amino]propyl}phenol [0186] Step 2: A mixture of alcohol 12 (1.20 g, 7.74 mmol), K2CO3 (1.18 g, 8.52 mmol), and benzyl bromide (1.10 mL, 9.29 mmol) in acetone (20 mL) was heated under reflux for 2 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc (100 mL), and washed with H2O and saturated NaCl. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification by flash chromatography (silica, 1:1 EtOAc:hexanes) gave alcohol 13 (1.15 g, 62%) as a white solid: 1H NMR (500 MHz, CDCl3) ? 7.43-7.25 (m, 5H), 7.11 (d, J=6 Hz, 2H), 6.91 (d, J=6 Hz, 2H), 5.04 (s, 2H), 3.67 (dd, J=6 Hz, 2H), 2.65 (t, J=6 Hz, 2H), 1.88 (n, 2H), 1.21 (t, J=6 Hz, 1H).
	With potassium carbonate In acetone	17 Preparation 17, 3-(4-Benzyloxyphenyl)propan-1-ol Preparation 17 3-(4-Benzyloxyphenyl)propan-1-ol To a solution of 3-(4-hydroxyphenyl)propan-1-ol (5g, 33mmol) and benzyl bromide (5.1ml, 42.9mmol) in acetone (100 ml) was added potassium carbonate (11.86g, 85.8 mmol). The mixture was then heated at reflux with vigorous stirring for 8 h. On cooling, the mixture was poured into water and extracted with diethyl ether (3 x 50ml). After drying over sodium sulfate, solvents were removed in vacuoand the solid residue recrystallized from ethanol/hexanes to afford the title compoundas a white solid (7.40g). 1 Nmr (CDCl3 δ: 1.40 (1H, br. s), 1.89 (2H, m), 2.67 (2H, t, J=8 Hz), 3.68 (2H, t, J=6 Hz), 5.05 (2H, s), 6.91 (2H, d, J=9 Hz), 7.12 (2H, d, J=9 Hz), 7.42 (5H, m).

Reference： [1]Zhou, Qingqing; Reekie, Tristan A.; Abbassi, Ramzi H.; Venkata, Dinesh Indurthi; Font, Josep S.; Ryan, Renae M.; Rendina, Louis M.; Munoz, Lenka; Kassiou, Michael [Australian Journal of Chemistry, 2018, vol. 71, # 10, p. 789 - 797]
[2]Gharpure, Santosh J.; Vishwakarma, Dharmendra S.; Nanda, Santosh K. [Organic Letters, 2017, vol. 19, # 24, p. 6534 - 6537]
[3]Boulard, Lucie; Bouzbouz, Samir; Cossy, Janine; Franck, Xavier; Figadère, Bruno [Tetrahedron Letters, 2004, vol. 45, # 35, p. 6603 - 6605]
[4]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[5]Lee, Cheng-Hsia Angeline; Loh, Teck-Peng [Tetrahedron Letters, 2006, vol. 47, # 10, p. 1641 - 1644]
[6]Menzler, Stefan; Bikker, Jack A.; Horwell, David C. [Tetrahedron Letters, 1998, vol. 39, # 41, p. 7619 - 7622]
[7]Current Patent Assignee: PFIZER INC - US2003/225164, 2003, A1 Location in patent: Page 11-12
[8]Current Patent Assignee: GLAXOSMITHKLINE PLC - EP711271, 1998, B1

15
[ 10210-17-0 ]
[ 143422-89-3 ]
[ 215776-67-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol; (2-methylallyl)tertiobutyl-dimethylsilane With scandium tris(trifluoromethanesulfonate) In various solvent(s) at 20℃; for 4h; Stage #2: With water In various solvent(s) at 20℃; for 3h;

Reference： [1]Suzuki; Watahiki; Oriyama [Tetrahedron Letters, 2000, vol. 41, # 46, p. 8903 - 8906]

16
[ 10210-17-0 ]
[ 870-63-3 ]
[ 410087-93-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;

Reference： [1]Vatèle, Jean-Michel [Tetrahedron, 2002, vol. 58, # 28, p. 5689 - 5698]

17
[ 10210-17-0 ]
[ 74-88-4 ]
[ 5406-18-8 ]

Yield	Reaction Conditions	Operation in experiment
94.9%	With potassium carbonate In acetone
94.93%	With potassium carbonate In diethyl ether; acetone	Preparation of 3-(4-methoxyphenl)-1-propanol Preparation of 3-(4-methoxyphenl)-1-propanol 2.26 g (14.87 mmoles) of 3-(4-hydroxyphenyl)-1-propanol were dissolved in dry acetone (20 ml) and potassium carbonate (2.05 g, 14.87 mmoles) was added, followed by methyl iodide (MeI) (2.11 g, 14.87 mmoles). The mixture was kept at reflux in a water bath at 60-70° C. for 48 h. After that period of time, it was diluted with water and the acetone was removed at reduced pressure. Extraction was performed with diethyl ether, and the result was washed with water, dried over sodium sulphate, filtered and the solvent was evaporated in a vacuum to give an oil (2.35 g) (94.93% yield) of 3-(4-methoxyphenyl)-1-propanol.

Reference： [1]González, Antonio G.; Silva, Margarita Hernández; Padrón, Juan I.; León, Francisco; Reyes, Eduardo; Álvarez-Mon, Melchor; Pivel, Juan P.; Quintana, José; Estévez, Francisco; Bermejo, Jaime [Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2358 - 2361]
[2]Current Patent Assignee: GOVERNMENT OF SPAIN - US2003/199575, 2003, A1

18
[ 10210-17-0 ]
[ 179548-39-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen iodide at 100℃;
32%	With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 5h;
	With hydrogen iodide

Reference： [1]Itsenko, Oleksiy; Langstroem, Bengt [Journal of Organic Chemistry, 2005, vol. 70, # 6, p. 2244 - 2249]
[2]Zhou, Fang; Zhu, Jin; Zhang, Yao; Zhu, Shaolin [Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4058 - 4062][Angew. Chem., 2018, vol. 130, p. 4122 - 4126,5]
[3]Lecarme, Laureline; Prado, Enora; De Rache, Aurore; Nicolau-Travers, Marie-Laure; Bonnet, Romaric; Heyden, Angeline Van Der; Philouze, Christian; Gomez, Dennis; Mergny, Jean-Louis; Jamet, Hlne; Defrancq, Eric; Jarjayes, Olivier; Thomas, Fabrice [Inorganic Chemistry, 2014, vol. 53, # 23, p. 12519 - 12531]

19
[ 1445-45-0 ]
[ 10210-17-0 ]
[ 80373-18-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With chloro-trimethyl-silane In dichloromethane at 20℃; for 4h;

Reference： [1]Sabitha, Gowravaram; Subba Reddy, Basi V.; Kiran Kumar Reddy, Garudammagari S.; Yadav, Jhillu S. [New Journal of Chemistry, 2000, vol. 24, # 2, p. 63 - 64]

20
Triton(R) X-405 (reduced) mesylate [ No CAS ]
[ 10210-17-0 ]
Triton(R) X-405 (reduced) supported 3-(4-hydroxyphenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With caesium carbonate In N,N-dimethyl-formamide at 55℃; for 46h;

Reference： [1]Benaglia, Maurizio; Cinquini, Mauro; Cozzi, Franco; Celentano, Giuseppe [Organic and Biomolecular Chemistry, 2004, vol. 2, # 22, p. 3401 - 3407]

21
[ 10210-17-0 ]
[ 990-91-0 ]
3-[4-(dibenzyl)phosphoryloxy]phenyl-1-propanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrahexylammonium iodide; silver(l) oxide In dichloromethane at 20℃; for 20h;

Reference： [1]Takeda, Shuzo; Chino, Masao; Kiuchi, Masatoshi; Adachi, Kunitomo [Tetrahedron Letters, 2005, vol. 46, # 31, p. 5169 - 5172]

22
[ 23795-02-0 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1h;Inert atmosphere;	General procedure: To astirred suspension of LiAlH4 (1.5 equiv) in THF (0.4 M) was addeddropwise a solution of ester derivative (1.0 equiv) in THF (0.3 M) at 0 C. Thereaction mixture was stirred under argon from 0 C to rt for 1 h. The reaction mixture was then added H2O,conc. HCl and extracted with EtOAc (x3). The combined organic layers were washed with brine, dried with anhydrous Na2SO4and concentrated in vacuo. Purification of the crude residue by columnchromatography gave the corresponding alcohol derivative.
68%		A suspension of LAH (10.5 g, w/w) in dry THF (500 mL) was refluxed for 3 hr. A solution of ethyl 3- (4-hydroxyphenyl) propionate (10 g, 1 eq, 55. 55 mmol) in dry THF (50 mL) was added drop wise at reflux temperature. After the addition, reaction mixture was refluxed for 6 hr. Reaction mixture was quenched with ethyl acetate (40mL, 4 eq with respect to LAH), followed by the addition of saturated Na2SO4 solution. To the workup mixture conc. HCI was added to adjust the pH at 7.0. Then reaction mixture was filtered through celite and washed with ethyl acetate. Combined filtrate was dried (Na2SO4), condensed, and the residue was chromatographed using ethyl acetate and hexane to obtain the title compound as white solid (5.7 g, 68 % yield). Mp: 52-54C. 'H NMR (CDC, 200 MHz) 8 : 1. 78-1.86 (m, 2H); 2.63 (t, J=7.9 Hz, 2H); 3.67 (t, J= 6. 3 Hz, 2H); 6.74 (d, J= 8.8 Hz, 2H); 7.05 (d, J= 8.8 Hz, 2H). IR (neat) cm-1 : 3485,3029, 2940, and 1505. Mass m/z (CI) : 152 [M+1].

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3505 - 3509
[2]Patent: WO2005/40102,2005,A2 .Location in patent: Page/Page column 55-56
[3]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 855 - 871
[4]European Journal of Medicinal Chemistry,1999,vol. 34,p. 919 - 937

23
[ 10210-17-0 ]
[ 910303-09-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With iodine; silver sulfate In dichloromethane at 20℃; for 24h;
59%	With [bis(pyridine)iodine]⁺ tetrafluoroborate; trifluoroacetic acid In acetonitrile at -10℃; for 0.25h; Schlenk technique; Inert atmosphere;
	With iodine; silver sulfate In methanol at 20℃; for 0.5h; Inert atmosphere;	77-78.A To a solution of 4-(3-hydroxypropyl)phenol (2.00 g, 13.14 mmol) in MeOH (10 ml) under nitrogen at RT was added silver sulfate (4.10 g, 13.14 mmol) followed by iodine (3.34 g, 13.14 mmol). The resulting mixture was stirred at room temperature for 30 minutes, then, the solids were filtered washing with MeOH. The filtrate was concentrated and purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the title compound, .H NMR (500 MHz, CD3OD): 6 7.51 (d, J- 2.1 Hz, 1 H); 7.02-6.97 (m, 1 H); 6.73 (d, J - 8.2 Hz, 1 H); 3.53 (t, J - 6.5 Hz, 2 H); 2.59-2.51 (m, 2 H); 1.80-1.71 (m, 2 H).

Reference： [1]Ghirmai, Senait; Mume, Eskender; Lundqvist, Hans; Tolmachev, Vladimir; Sjoeberg, Stefan [Journal of labelled compounds and radiopharmaceuticals, 2005, vol. 48, # 12, p. 855 - 871]
[2]Švec, Pavel; Nový, Zbyněk; Kučka, Jan; Petřík, Miloš; Sedláček, Ondřej; Kuchař, Martin; Lišková, Barbora; Medvedíková, Martina; Kolouchová, Kristýna; Groborz, Ondřej; Loukotová, Lenka; Konefał, Rafał Ł.; Hajdúch, Marián; Hrubý, Martin [Journal of Medicinal Chemistry, 2020, vol. 63, # 24, p. 15960 - 15978]
[3]Current Patent Assignee: MERCK & CO INC - WO2012/58187, 2012, A1 Location in patent: Page/Page column 103

24
[ 10210-17-0 ]
MeO-(CH₂CH₂O)nCH₂CH₂-O-p-C₆H₄(CH₂)3OH, n = ca. 110 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 40h;

Reference： [1]Benaglia, Maurizio; Guizzetti, Stefania; Rigamonti, Clara; Puglisi, Alessandra [Tetrahedron, 2005, vol. 61, # 51, p. 12100 - 12106]

25
[ 67-56-1 ]
[ 10210-17-0 ]
4-(3-hydroxypropyl)-4-methoxycyclohexa-2,5-dienone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With [bis(acetoxy)iodo]benzene at 20℃; for 2h;
	With [bis(acetoxy)iodo]benzene at 20℃;
	With [bis(acetoxy)iodo]benzene at 0 - 20℃; for 2h;

Reference： [1]Liu, Qin; Rovis, Tomislav [Journal of the American Chemical Society, 2006, vol. 128, # 8, p. 2552 - 2553]
[2]Canesi, Sylvain; Mammasse, Zahra; Signo, Kouassi [Journal of Organic Chemistry, 2020, vol. 85, # 4, p. 2832 - 2837]
[3]Tamanna; Hussain, Yaseen; Sharma, Deepak; Chauhan, Pankaj [Journal of Organic Chemistry, 2022, vol. 87, # 9, p. 6397 - 6402]

26
[ 10210-17-0 ]
[ 3747-74-8 ]
3-[4-(quinolin-2-ylmethoxy)-phenyl]-propan-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 690 - 705

27
[ 10210-17-0 ]
[ 897025-81-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With Oxone; sodium hydrogencarbonate In water at 25℃; for 0.25h;
36%	With Oxone; sodium hydrogencarbonate In water

Reference： [1]Carreno, M. Carmen; Gonzalez-Lopez, Marcos; Urbano, Antonio [Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2737 - 2741]
[2]Eske, Angelika; Ecker, Sabrina; Fendinger, Carolina; Goldfuss, Bernd; Jonen, Matthis; Lefarth, Jens; Neudörfl, Jörg-M.; Spilles, Matthias; Griesbeck, Axel G. [Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13770 - 13774][Angew. Chem., 2018, vol. 130, p. 13966 - 13970,5]

28
[ 10210-17-0 ]
[ 1609-47-8 ]
carbonic acid ethyl ester 4-(3-hydroxy-propyl)-phenyl ester [ No CAS ]
3-{4-[(ethoxycarbonyl)oxy]phenyl}propyl ethyl dicarbonate [ No CAS ]
ethyl 3-(4-hydroxyphenyl)propyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With magnesium(II) perchlorate In dichloromethane at 40℃; for 6h;

Reference： [1]Bartoli, Giuseppe; Bosco, Marcella; Carlone, Armando; Locatelli, Manuela; Marcantoni, Enrico; Melchiorre, Paolo; Palazzi, Paolo; Sambri, Letizia [European Journal of Organic Chemistry, 2006, # 19, p. 4429 - 4434]

29
[ 10210-17-0 ]
[ 2616-64-0 ]
3-(4'-hydroxyphenyl)propanol 4'-O-β-D-glucuronide [ No CAS ]
3-(4'-hydroxyphenyl)propanol 1-O-β-D-glucuronide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 56% 2: 5.5%	With Tris-HCl buffer; calcium chloride; diothiothreitol In water; dimethyl sulfoxide at 35℃; for 8h; Enzymatic reaction;

Reference： [1]Khymenets, Olha; Joglar, Jesus; Clapes, Pere; Parella, Teodor; Covas, Maria-Isabel; De La Torre, Rafael [Advanced Synthesis and Catalysis, 2006, vol. 348, # 15, p. 2155 - 2162]

30
[ 629-04-9 ]
[ 10210-17-0 ]
[ 1000508-51-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide In ethanol	3 Compound 12 is prepared using the route outlined in Scheme 6, starting with 4-(3- hydroxypropyl)phenol (Aldrich Chemical Company) and initially following the procedure of Kiuchi, M., et al (2000). Compound 12 is obtained as an off white solid and of broad melting point.

Reference： [1]Current Patent Assignee: OPKO HEALTH INC - WO2008/31032, 2008, A2 Location in patent: Page/Page column 38-39; 49

31
[ 10210-17-0 ]
[ 1439-36-7 ]
[ 952315-71-8 ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃; for 0.25h; Stage #2: 1-triphenylphosphoranylidene-2-propanone In dichloromethane at -78 - 20℃; Further stages.;

Reference： [1]Grant, Tina N.; West [Organic Letters, 2007, vol. 9, # 19, p. 3789 - 3792]

32
[ 106-41-2 ]
[ 10210-17-0 ]
[ 19249-03-7 ]
3-(4-(2-(2-(2-(4-bromophenoxy)ethoxy)ethoxy)ethoxy)phenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: 4-bromo-phenol; 3-(4-hydroxyphenyl)propan-1-ol With sodium ethanolate In acetonitrile at 20℃; for 0.5h; Stage #2: triethylene glycol di-(p-toluenesulfonate) In acetonitrile for 5h; Heating; Further stages.;

Reference： [1]Abraham, Werner; Buck, Karin; Orda-Zgadzaj, Marziena; Schmidt-Schaeffer, Sebastian; Grummt, Ulrich-W. [Chemical Communications, 2007, # 29, p. 3094 - 3096]

33
[ 10210-17-0 ]
[ 767330-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 80 percent / Ag₂O / CH₂Cl₂ / 0 °C 2: 76 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C 3: CSA / CH₂Cl₂ / 15 °C
	Multi-step reaction with 3 steps 1: 90 percent / NaH / dimethylformamide / 12 h / Heating 2: 100 percent / PCC / CH₂Cl₂ / 20 °C 3: 61 percent / diethyl ether / -78 °C
	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 1.5 h / 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / di-isopropyl ether / 24 h / 30 °C / Inert atmosphere; Enzymatic reaction

	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 1.5 h / 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / tetrahydrofuran / 20 h / 30 °C / Inert atmosphere; Enzymatic reaction 5.1: potassium carbonate / methanol / 1 h / 20 °C
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 1.5 h / 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / di-isopropyl ether / 17 h / 20 °C / Inert atmosphere; Enzymatic reaction 5.1: potassium carbonate / methanol / 1 h / 20 °C
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 1.5 h / 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / di-isopropyl ether / 24 h / 30 °C / Inert atmosphere; Enzymatic reaction 5.1: potassium carbonate / methanol / 1 h / 20 °C
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 1.5 h / 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / acetonitrile / 65 h / 30 °C / Inert atmosphere; Enzymatic reaction 5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 10 h / -30 °C / Inert atmosphere 6.1: potassium carbonate / methanol / 0.25 h / 0 - 20 °C
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 1.5 h / 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / di-isopropyl ether / 17 h / 20 °C / Inert atmosphere; Enzymatic reaction 5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 10 h / -30 °C / Inert atmosphere 6.1: potassium carbonate / methanol / 0.25 h / 0 - 20 °C
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetone / 10 h / Reflux; Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: zinc / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 1.5 h / 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / di-isopropyl ether / 24 h / 30 °C / Inert atmosphere; Enzymatic reaction 5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 10 h / -30 °C / Inert atmosphere 6.1: potassium carbonate / methanol / 0.25 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: potassium carbonate / ethanol / 6 h / Inert atmosphere; Reflux 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; caesium carbonate; 3-nitrobenzoic acid / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Glovebox

Reference： [1]Lee, Cheng-Hsia Angeline; Loh, Teck-Peng [Tetrahedron Letters, 2006, vol. 47, # 10, p. 1641 - 1644]
[2]Boulard, Lucie; Bouzbouz, Samir; Cossy, Janine; Franck, Xavier; Figadère, Bruno [Tetrahedron Letters, 2004, vol. 45, # 35, p. 6603 - 6605]
[3]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[4]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[5]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[6]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[7]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[8]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[9]Tadiparthi, Krishnaji; Raghavendra; Kamal, Ahmed [Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2321 - 2326]
[10]Klucznik, Tomasz; Mikulak-Klucznik, Barbara; McCormack, Michael P.; Lima, Heather; Szymkuć, Sara; Bhowmick, Manishabrata; Molga, Karol; Zhou, Yubai; Rickershauser, Lindsey; Gajewska, Ewa P.; Toutchkine, Alexei; Dittwald, Piotr; Startek, Michał P.; Kirkovits, Gregory J.; Roszak, Rafał; Adamski, Ariel; Sieredzińska, Bianka; Mrksich, Milan; Trice, Sarah L.J.; Grzybowski, Bartosz A. [Chem, 2018, vol. 4, # 3, p. 522 - 532]

34
[ 24807-40-7 ]
[ 10210-17-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1982,p. 2051 - 2058

35
[ 7400-08-0 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With whole cell cultures of dichomitus albidofuscus at 24℃; for 72h; Darkness; Microbiological reaction;	2.5. general procedure for preparative biotransformation General procedure: The substrate (1 mmol) was added to submerged cultures of DAL on the 3rd culture day. The reaction mixture was incubated on an incubation shaker at 150 rmin 1 (deflection 25 mm) under exclusion of light at 24 °C for 4 days. 10 g of NaCl was added to media, and the mixture was stirred for 10 min at 800 rpm (magnetic stirrer). For extraction, 50 mL of Et2O was added, and the resulting mixture was stirred for 20 min at 800 rpm (magnetic stirrer), and centrifuged for 5 min at 3000 × g to separatethe organic layer. The extraction was repeated three times. The combined organic layers were washed with brine (1 × 30 mL) and water (1× 30 mL), dried over Na2SO4 and evaporated to dryness. The resulting reaction mixtures were analysed by GC/MS and NMR spectroscopy.Products were purified by column chromatography on silica gel (eluent(pentane/ether) changed gradually: 10/1, 7/3, 1/1) to isolate the majorcomponents. The respective fractions were combined, concentrated in vacuum, and the 1H and 13C NMR spectra of the residuals were compared with those of reference compounds. Every biotransformation was repeated three times to verify the reproducibility of the experiments. The detailed information about experimental data and yields is provided in the Electronic Supplementary Information.
	Multi-step reaction with 3 steps 1: aq. HCl / 6 h / Heating 2: H₂ / 10percent Pd/C / methanol / 0.5 h / 760 Torr / Ambient temperature 3: LiBH₄ / diethyl ether; toluene / 0.25 h / Heating
	Multi-step reaction with 4 steps 1.1: pyridine / 1 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / 1,4-dioxane / 1 h / Inert atmosphere 2.2: 1 h / Inert atmosphere 3.1: potassium hydroxide / ethanol / 8 h / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 2250.23 Torr

Reference： [1]Zhuk, Tatyana S.; Skorobohatko, Oleksandra S.; Albuquerque, Wendell; Zorn, Holger [Bioorganic Chemistry, 2021, vol. 108]
[2]Lam, Thi Bach Tuyet; Iiyama, Kenji; Stone, Bruce A. [Phytochemistry, 1992, vol. 31, # 4, p. 1179 - 1184]
[3]Current Patent Assignee: FUJIFILM HOLDINGS CORP.; DAINIPPON KASEI - JP2016/132639, 2016, A

36
[ 10210-17-0 ]
[ 106-94-5 ]
3-(4-propoxyphenyl)-1-propanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sodium chloride; potassium carbonate In water; acetone	R.169 Reference Example 169 Reference Example 169 A mixture of 3-(4-hydroxyphenyl)-1-propanol (1.33 g), 1-bromopropane (1.2 ml) and potassium carbonate (2.25 g) and acetone (100 ml) was heated at reflux for 2 days. After concentration under reduced pressure, the residue was mixed with water and was extracted with ethyl acetate. The organic layer was washed with a 1 N aqueous solution of sodium hydroxide and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3-(4-propoxyphenyl)-1-propanol (1.61 g) as a colorless oily substance. 1H-NMR (200 MHz, CDCl3) δ1.03 (3H, t, J=7.5 Hz), 1.70-1.91 (4H, m), 2.61-2.69 (3H, m), 3.67 (2H, t, J=6.5 Hz), 3.90 (2H, t, J=6.6 Hz), 6.83 (2H, d, J=8.4 Hz), 7.10 (2H, d, J=8.4 Hz).
1.61 g	With potassium carbonate In acetone for 48h; Heating / reflux;

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US6627651, 2003, B1
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1182195, 2002, A1 Location in patent: Example 169

37
[ 10210-17-0 ]
[ 2567-29-5 ]
[ 712313-40-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium carbonate; In propyl cyanide; at 120℃; for 6h;	12.8 g (41.4 mmol) 4-Phenylbenzylbromid, 6.94 g (45.6 mmol) 4-Hydroxy- phenylpropanol und 6.87 g (49.7 mmol) Kaliumcarbonat werden in 50 ml Butyronitril 6 Stunden bei 120-'C GERHRT. Nach dem Abkhlen auf Raumtemperatur wird von den anorganischen Salzen abgesaugt und im Vakuum eingeengt. Das ROHPRODUKT WIRD BER 60 (LAUFMITTELGRADIENT CYCLOHEXAN --> Cyclohexan/Ethylacetat 60 : 40) chromatographisch gereinigt. Man ERHLT 4. 90 g (37 % d. Th. ) Produkt. Fp. : 128 C. HPLC (Methode 1) : Rt : 5.12 min. IH-NMR (300 MHz, DMSO-D6, 8/PPM) : 7.70-7. 64 (m, 4H), 7.55-7. 42 (m, 4H), 7.40- 7.33 (m, 1H), 7.11 (d, 2H), 6.93 (d, 2H), 5.11 (s, 2H), 4.39 (t, 1H), 3.39 (m, 2H), 2.53 (m, 2H), 1.67 (quint, 2H). MS (DCI) : m/z = 336 (M+NH4+).

Reference： [1]Patent: WO2004/52839,2004,A1 .Location in patent: Page 63

38
[ 10210-17-0 ]
[ 124-63-0 ]
[ 251978-03-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
61%	With triethylamine In dichloromethane at 0 - 20℃; for 16h;	1.ii Step (ii) To a DCM (550 mL) solution of 3-(4-hydroxyphenyl)propanol (17 g, 1.0 eq, 111.8 mmol), obtained in the step (i) and triethylamine (93.3 mL, 6.0 eq, 670.8 mmol) was added methanesulfonyl chloride (26 mL, 3.0 eq, 335.4 mmol) dropwise at 0° C. The reaction mixture was stirred at RT for 16 h, after that it was worked up by diluting with excess DCM and washing the organic layer with dil. HCl, water and brine. The organic layer was dried (Na2SO4) and concentrated. Desired product from the crude mass was purified by recrystallization from diisopropylether. The remaining mother liquor was condensed and was chromatographed (ethyl acetate/hexanes) to obtain further amount desired compound (total yield 20.8 g, 61%) as white solid. Mp: 60-62° C. 1H NMR (CDCl3, 200 MHz: δ 2.00-2.18 (m, 2H); 2.77 (t, J=7.8 Hz, 2H); 3.00 (s, 3H); 3.13 (s, 3H); 4.23 (t, J=6.3 Hz, 2H); 7.22 (aromatics, 4H). IR (neat) cm-1: 3029, 2935, 1504. Mass m/z (CI): 309 [M+1].
61%	With triethylamine In dichloromethane at 0 - 20℃; for 16h;	ii Step (ii) To a DCM (550 mL) solution of 3-(4-hydroxyphenyl)propanol (17 g, 1.0 eq, 111.8 mmol), obtained in the step (i) and triethylamine (93.3 mL, 6.0 eq, 670.8 mmol) was added methanesulfonyl chloride (26 mL, 3.0 eq, 335.4 mmol) dropwise at 0° C. The reaction mixture was stirred at RT for 16 h, after that it was worked up by diluting with excess DCM and washing the organic layer with dil. HCl, water and brine. The organic layer was dried (Na2SO4) and concentrated. Desired product from the crude mass was purified by recrystallization from diisopropylether. The remaining mother liquor was condensed and was chromatographed (ethyl acetate/hexanes) to obtain further amount desired compound (total yield 20.8 g, 61%) as white solid. Mp: 60-62° C. [0186] 1H NMR (CDCl3, 200 MHz: δ2.00-2.18 (m, 2H); 2.77 (t, J=7.8 Hz, 2H); 3.00 (s, 3H); 3.13 (s, 3H); 4.23 (t, J=6.3 Hz, 2H); 7.22 (aromatics, 4H). [0187] IR (neat) cm-1: 3029, 2935, 1504. [0188] Mass m/z (CI): 309 [M+1].

Reference： [1]Liang, Huan; Ciufolini, Marco A. [Chemistry - A European Journal, 2010, vol. 16, # 44, p. 13262 - 13270]
[2]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2005/277693, 2005, A1 Location in patent: Page/Page column 5-6
[3]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2003/229083, 2003, A1 Location in patent: Page 19-20

39
[ 10210-17-0 ]
[ 98-59-9 ]
3-(4-(tosyloxy)phenyl)propyl 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.7%	With triethylamine In dichloromethane at 0 - 20℃; for 16h;	To a solution of 3-(4-hydroxyphenyl)propanol (2.5 g, 1.0 eq, 16.44 mmol), obtained in the step (i) of preparation 1 in DCM (82 mL) and triethylamine (11.4 mL, 5.0 eq, 82.2 mmol), was added toluene-4-sulfonylchloride (9.4 g, 3.0 eq, 49.3 mmol) dropwise at 0° C. The reaction mixture was stirred at RT for 16 h, after that it was worked up by diluting with excess DCM and washing the organic layer with water and brine. The crude residue obtained after drying (Na2SO4) and condensing was chromatographed (ethyl acetate/hexanes) to obtain the desired compound (5.1 g, 67.7%) as thick liquid. [0201] 1H NMR (CDCl3, 200 MHz: δ 1.90 (quintet, J=7.9 Hz, 2H); 2.44 (s, 6H); 2.61 (t, J=6.8 Hz, 2H); 3.98 (t, J=6.3 Hz, 2H); 6.83 (d, J=8.8 Hz, 2H); 6.97 (d, J=8.8 Hz, 2H); 7.32 (t, J=7.5 Hz, 2H); 7.67 (d, J=8.3 Hz, 2H); 7.76 (d, J=8.3 Hz, 2H). [0202] IR (neat) cm-1: 2926, 1597, 1502, 1364. [0203] Mass m/z (CI): 461 [M+1].
	With pyridine at 0℃; for 8.16667h;

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2003/229083, 2003, A1 Location in patent: Page 20
[2]Yang, Chu-Ting; Zhang, Zhen-Qi; Liu, Yu-Chen; Liu, Lei [Angewandte Chemie - International Edition, 2011, vol. 50, # 17, p. 3904 - 3907]

40
[ 10210-17-0 ]
[ 99103-80-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride In water at 100℃; for 14h;	79.a Example 79.; 3- [4- (3-CHLOROPROPYL) PHENOXY]-2-HYDROXY-2-METHYL-N- (3-METHYL-4-NITRO- phenyl) propionamide; a) 4- (3-CHLOROPROPYL) phenol 3- (4-HYDROXYPHENYL)-L-PROPANOL (0.97 g, 0.006374 mol) and concentrated HCl (20 ml) were heated at 100 °C for 14 h. After being cooled, the reaction mixture was poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and concentrated in vacuo to give a raw product. Purification by flash chromatography (heptane/ethyl acetate 9: 1) gave a pure product (0.98 g, 90%). H NMR (400 MHz, DMSO-d6) : 1.95 (2H, quintet, 3J= 7.0 Hz), 2.59 (2H, t, 3J= 7.5 Hz), 3. 58 (2H, t, 3J= 6.5 Hz), 6.67 (2H, d, 3J = 8. 2 Hz), 6.99 (2H, d, 3J = 8. 2 Hz), 9.15 (1H, s, -OH).
78%	With thionyl chloride; triethylamine In dichloromethane at 0 - 40℃; for 14h;
74%	With thionyl chloride In dichloromethane at 0 - 20℃; for 16h; Reflux;	Analogous to a literature protocol.[2] 3-4(hydroxyphenyl)-1-propanol (1.0 g, 6.6mmol) andtriethylamine (0.92 ml, 6.6 mmol) were dissolved in dichloromethane (15 ml) and cooled to 0°C. Thionyl chloride (0.48 ml, 6.6 mmol) was added drop-wise over 1 min. The reaction wasallowed to warm to room temperature and heated at reflux for 16 h. After this time, thereaction was allowed to cool to room temperature, water (20 ml) was added and organic andaqueous layers separated. The aqueous layer was extracted with dichloromethane (2 x 20 ml).The organic layers were combined and washed with saturated aqueous sodium hydrogencarbonate (10 ml) and brine (10 ml). The organic layers were dried over MgSO4, filtered andreduced to dryness to give the title compound (0.82g, 74%) after column chromatography(10:90 ethyl acetate : pentane); 1H NMR (500 MHz, CDCl3): δ 7.05 (d, J = 8.4 Hz, 2H), 6.76(d, J = 8.4 Hz, 2H), 3.51 (t, J = 6.5 Hz, 2H), 2.70 (t, J = 7.4 Hz, 2H), 2.06-2.00 (m, 2H); 13CNMR (125 MHz, CDCl3):153.9, 133.0, 129.8, 115.4, 44.4, 34.3, 31.9; HRMS (EI) calculatedfor C9H11OCl [M]+: 170.049847; found: 170.049770.

With thionyl chloride; triethylamine In dichloromethane at 20℃; for 1.5h;

Reference： [1]Current Patent Assignee: ORION OYJ - WO2005/794, 2005, A1 Location in patent: Page 53
[2]Pulido, Daniel; Casadó-Anguera, Verònica; Gómez-Autet, Marc; Llopart, Natàlia; Moreno, Estefanía; Casajuana-Martin, Nil; Ferré, Sergi; Pardo, Leonardo; Casadó, Vicent; Royo, Miriam [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 616 - 632]
[3]Jones, Kevin M.; Hillringhaus, Tim; Klussmann, Martin [Tetrahedron Letters, 2013, vol. 54, # 25, p. 3294 - 3297]
[4]Shen, Yanhong; Sheng, Rong; Zhang, Jing; He, Qiaojun; Yang, Bo; Hu, Yongzhou [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 16, p. 7646 - 7653]

41
[ 600-00-0 ]
[ 10210-17-0 ]
ethyl 2-[4-(3-hydroxypropyl)phenoxy]-2-methylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate In ethanol at 70℃; for 17h;	16.2 A mixture of 3- (4-hydroxyphenyl) propan-1-ol (3 g, 1 eq, 19.74 mmol), obtained in step 1 of preparation 16, ethyl 2-bromoisobutyrate (8.69 mL, 3 eq, 59.21 mmol), and powdered anhydrous K2CO3 (13.6 g, 5 eq, 98.7 mmol) in EtOH (98 mL) was heated at 70 °C for 17 h. Reaction mixture was condensed to dryness, diluted with ethyl acetate (200 mL) and washed with water (2x100 mL). Organic layer was dried (Na2SO4), condensed, and the residue was chromatographed using ethyl acetate and hexane to obtain the title compound as thick mass (4.7 g, 89 % yield). 'H NMR (CDC13, 200 MHz) 8 : 1.25 (t, J= 7. 2 Hz, 3H) ; 1.57 (s, 6H); 1.82-1. 89 (m, 2H); 2.64 (t, J= 7.2 Hz, 2H) ; 3.65 (. t, J= 6.4 Hz, 2H); 4.23 (q, J= 7.2 Hz, 2H); 6.77 (d, J= 8.8 Hz, 2H); 7.05 (d, J= 8.8 Hz, 2H) IR (neat) cm'' : 3406,2939, 1733, and 1509. Mass m/z (CI): 267 [M+1].
73%	With potassium carbonate In N,N-dimethyl-formamide Reflux;	Ethyl 2-[4-(3-hydroxypropyl)phenoxy]-2-methylpropanoate (13) General procedure: The ethyl 2-bromo-2-methylpropanoate (22.3 mmol, 3.3 mL) wase added to a solution of 4-(hydroxymethyl)phenol (8), 4-(2-hydroxyethyl)phenol (9) or 4-(3-hydroxypropyl)phenol (10) (7.2 mmol) and dry K2CO3 (72.0 mmol, 9.96 g) dissolved in DMF (3 mL/mmol, 21.7 mL). After stirring for 4-5 h at reflux, the reaction was quenched with water (25 mL) and the mixture extracted with ethyl acetate (3 × 50 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent cyclohexane/ethyl acetate 8:2).

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2005/40102, 2005, A2 Location in patent: Page/Page column 56
[2]Giampietro, Letizia; D'Angelo, Alessandra; Giancristofaro, Antonella; Ammazzalorso, Alessandra; De Filippis, Barbara; Fantacuzzi, Marialuigia; Linciano, Pasquale; MacCallini, Cristina; Amoroso, Rosa [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7662 - 7666]

42
[ 6271-78-9 ]
[ 10210-17-0 ]
[ 676493-92-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In 2,2,4-trimethylpentane; ISOPROPYLAMIDE; for 6h;Heating / reflux;	Add potassium carbonate (2. 2821 g, 16.51 mmol) to a stirred solution OF 3- (4- HYDROXYPHENYL)-1-PROPANOL (1.0041 g, 6.598 mmol), 6-CHLORONICOTINAMIDE (1.0038 g, 6.411 mmol). dimethylacetamide (21 ML), AND isooctane (3 mL). Equip the reaction setup with a Dean-Stark trap and heat the reaction to reflux under nitrogen for 6 h. Cool the reaction to room temperature and filter off the solids. Concentrate on a rotary evaporator to give the crude product. Take the crude product up in 1 N sodium hydroxide (250 mL), extract with ethyl acetate (4 X 100 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 1.5% concentrated ammonium hydroxide/15% ethanol/chloroform to yield 1.5188 g (87%) of 6-[4-(3- HYDROXY-PROPYL)-PHENOXY]-NICOTINAMIDE : mass spectrum (ion spray): m/z = 273.2 (M+1) ; 'H NMR (DMSO-d6) : 8.61 (d, 1H), 8.24 (dd, 1H), 8.03 (s, 1H), 7.48 (s, 1H), 7.25 (d, 2H), 7.07-7. 03 (m, 3H), 4.50 (t, 1H), 3.46-3. 41 (m, 2H), 2.63 (t, 2H), 1.77-1. 70 (m, 2H).

Reference： [1]Patent: WO2004/26305,2004,A1 .Location in patent: Page/Page column 113-114

43
[ 10210-17-0 ]
[ 124-63-0 ]
4-(3-methanesulfonyloxypropyl)phenylmethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine In dichloromethane at 0 - 20℃; for 16h;	1.ii Step (ii); To a DCM (550 mL) solution of 3-(4-hydroxyphenyl)propanol (17 g, 1.0eq, 111.8 mmol), obtained in the step (i) and triethylamine ( 93.3 mL, 6.0 eq, 670.8mmol) was added methanesulfonyl chloride ( 26 mL, 3.0 eq, 335.4 mmol) dropwise at0°C. The reaction mixture was stirred at RT for 16 h, after that it was worked up bydiluting with excess DCM and washing the organic layer with dil. HC1, water and brine.The organic layer was dried (N^SO/O and concentrated. Desired product from the crudemass was purified by recrystallization from diisopropylether. The remaining motherliquor was condensed and was chromatographed (ethyl acetate/hexanes) to obtainfurther amount desired compound (total yield 20.8 g, 61%) as white solid.Mp: 60-62°C..H NMR (CDC13, 200 MHz: 8 2.00-2.18 (m, 2H); 2.77 (t, J = 7.8 Hz,2H); 3.00 (s, 3H); 3.13 (s, 3H); 4.23 (t, J = 6.3 Hz, 2H); 7.22 (aromatics, 4H).IR (neat) cm'1: 3029, 2935, 1504.Mass m/z (CI): 309 [M + 1].

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2006/1795, 2006, A1 Location in patent: Page/Page column 12-13

44
ethyl 4-bromo-2-[[(phenylmethoxy)carbonyl]amino]butanoate [ No CAS ]
[ 10210-17-0 ]
O-[3-[3-[(aminoiminomethyl)hydrazono]propyl]phenyl]-N-[(phenylmethoxy)carbonyl]-homoserine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In acetonitrile	11 O-[3-[3-[(Aminoiminomethyl)hydrazono]propyl]phenyl]-N-[(phenylmethoxy)carbonyl]-homoserine Example 11 O-[3-[3-[(Aminoiminomethyl)hydrazono]propyl]phenyl]-N-[(phenylmethoxy)carbonyl]-homoserine Stage A: Ethyl O-[4-(3-Hydroxypropyl)phenyl]-N-[(phenylmethoxy)carbonyl]-homoserinate. The mixture constituted by 306 mg of 4-hydroxybenzenepropanol, 770 mg of ethyl 4-bromo-2-[[(phenylmethoxy)carbonyl]amino]butanoate and 740 mg of Cs2CO3 in 10 ml of acetonitrile is heated under reflux for 45 minutes, the solid is filtered, washed with dichloromethane then the filtrate is evaporated under reduced pressure until 1.5 g of crude product is obtained which is purified by chromatography on a silica column (Kieselgel 60; 40-63 μm) eluding with a dichloromethane/methanol mixture 95/5. 440 mg of expected product is obtained. IR (CHCl3) 3624 cm-1 (-OH); 3431 cm-1 (NH); 721 cm-1 (max. C=O); 1609, 1602, 1584, 1508 cm-1 (Aromatic+amide II).

Reference： [1]Current Patent Assignee: SANOFI; ROCHE HOLDING AG - US6391904, 2002, B1

45
2R-(-)-glycidyl-3-nitrobenzenesulfonate [ No CAS ]
[ 10210-17-0 ]
[ 15408-62-5 ]
[ 246218-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate In methanol; ethanol; water; acetone	7 Preparation of (R)-1-[1,1-Dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[(4-(3-hydroxy)propyl)phenoxy]-propan-2-ol Hydrochloride Salt EXAMPLE 7 Preparation of (R)-1-[1,1-Dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[(4-(3-hydroxy)propyl)phenoxy]-propan-2-ol Hydrochloride Salt A mixture of 3-p-hydroxyphenylpropanol (Aldrich, 1 g, 6.5 mmol), K2CO3 (1.1 g, 7.8 mmol), and 2R-(-)-glycidyl-3-nitrobenzenesulfonate (2.1 g, 8.2 mmol) in acetone (30 mL) was refluxed for 24 h. The mixture was cooled, concentrated, taken up in H2O and extracted with diethyl ether. The organic extracts were washed with 5% NaHCO3, brine, dried over MgSO4, filtered, and concentrated. This compound (0.35 g, 1.68 mmol), and 4-methoxyphenyl-1,1-dimethyl ethylamine (0.331 g, 1.89 mmol) in ethanol (10 mL) was heated at reflux for 24 h. The mixture was cooled, concentrated and purified by flash column chromatography (5% MeOH/CHCl3) to afford an oil which was stirred in methanol and added 4M HCl, concentrated and triturated in ether to give a white powder of the title compound (0.15 g). ESMS (M+H)+m/e 388.3.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US6395919, 2002, B1

46
[ 558-13-4 ]
[ 10210-17-0 ]
[ 52273-55-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine In dichloromethane	2.a EXAMPLE 2 (a). A mixture of 10 g of 3-(4-hydroxyphenyl)-1-propanol, 19 g of triphenylphosphine and 200 ml of dichloromethane was treated dropwise at --18° C. with a solution of 24 g of tetrabromomethane in 100 ml of dichloromethane. The reaction mixture was stirred at room temperature overnight and then concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 4:1). This gave 14 g of 3-(4-hydroxyphenyl)-1-propyl bromide.

Reference： [1]Current Patent Assignee: MERCK KGAA - US5204018, 1993, A

47
[ 10210-17-0 ]
[ 98-59-9 ]
p-(3-hydroxypropyl)phenyl p-tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane	20.a EXAMPLE 20 a) A solution of 400 mg of p-(3-hydroxypropyl)phenol and 0.421 ml of triethylamine in 2.6 ml of methylene chloride was treated portionwise at 0° C. with 539 mg of p-tosyl chloride and the mixture was stirred for a further 5 minutes at 0° C. and for 15 minutes at -5° C. Subsequently, the reaction mixture was diluted with water, made slightly acid with dilute hydrochloric acid and extracted three times with methylene chloride. The organic phases were washed twice with water, dried over magnesium sulphate and freed from solvent. The residual, colourless oil (870 mg) was purified by chromatography on silica gel with ethyl acetate/petroleum ether, whereby 693 mg (83%) of p-(3-hydroxypropyl)phenyl p-tosylate were isolated as a milky oil.
	With triethylamine In dichloromethane	10.a EXAMPLE 10 (a) A solution of 400 mg of p-(3-hydroxypropyl)phenol and 0.421 ml of triethylamine in 2.6 ml of methylene chloride was treated portionwise at 0° C. with 539 mg of p-tosyl chloride and the mixture was stirred for a further 5 minutes at 0° C. and for 15 minutes at -5° C. Subsequently, the reaction mixture was diluted with water, made slightly acid with dilute hydrochloric acid and extracted three times with methylene chloride. The organic phases were washed twice with water, dried over magnesium sulphate and freed from solvent. The residual, colourless oil (870 mg) was purified by chromatography on silica gel with ethyl acetate/petroleum ether, whereby 693 mg (83%) of p-(3-hydroxypropyl)phenyl p-tosylate were isolated as a milky oil.

Reference： [1]Current Patent Assignee: BASF SE - US5238602, 1993, A
[2]Current Patent Assignee: MERCK KGAA - US4709030, 1987, A

48
[ 111-25-1 ]
[ 10210-17-0 ]
[ 882691-17-0 ]

Yield	Reaction Conditions	Operation in experiment
77.6%	With sodium hydroxide In ethanol	3; 2 Scheme 2 illustrates a similar synthetic procedure for preparing of an analog having increased water solubility; Compound 23 was prepared using the route outlined in Scheme 2, starting with 4-(3-hydroxypropyl)phenol (Aldrich Chemical Company). Yields obtained are reported in Scheme 2. Compound 23 was obtained as an off white solid and melting point was broad. (M-1) molecular ion is 322.3 a.m.u. 1H NMR (CD3OD) δ: 0.95 (3H, tr), 1.37 (4H, m), 1.45 (2H, m), 1.75 (6H, m), 2.55 (2H, m), 3.7 (2H, dd), 3.9 (2H, t), 6.9 (4H, dd).

Reference： [1]Current Patent Assignee: OPKO HEALTH INC - US2006/79542, 2006, A1 Location in patent: Page/Page column 11; 17

49
[ 132769-09-6 ]
[ 10210-17-0 ]
4-(3-hydroxypropyl)phenyl 2-(6-methoxymethoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium thiosulfate In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water	R.20 4-(3-hydroxypropyl)phenyl 2-(6-methoxymethoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethyl ether STR50 REFERENCE EXAMPLE 20 4-(3-hydroxypropyl)phenyl 2-(6-methoxymethoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethyl ether STR50 Sodium hydride (185 mg) was added to a solution of 3-(4-hydroxyphenyl)propanol (560 mg) in tetrahydrofuran (6 ml). The mixture was stirred at room temperature under an atmosphere of argon. After the evolution of hydrogen finished, hexamethylphosphoramide (3 ml) was added to the solution. A solution of the tosyl compound (1.5 g), which was prepared with using the alcohol prepared in reference example 7 by the same procedure as reference example 18, in hexamethylphosphoramide (6 ml) was added dropwise to this solution. The solution was stirred at 80° C. all night. The reaction solution was permitted to stand for a moment. Water was added to the solution. The solution was slightly acidified with 2N hydrochloric acid and extracted with ethyl acetate (150 ml). The organic layer was washed with, in order, a saturated aqueous solution of sodium bicarbonate, an aqueous solution of sodium thiosulfate, water and then saturated brine, dried over anhydrous sodium sulfate and then evaporated. The residue was purified by column chromatography on silica gen (n-hexane: ethyl acetate=2:1) to give the title compound (1.22 g) having the following physical data. NMR: δ 7.09 (2H, d), 6.80 (2H, d), 4.86 (2H, s), 4.17 (2H, m), 3.66 (2H, q), 3.62 (3H, s), 3.63 (4H, m), 2.20 (3H, s), 2.15 (3H, s), 2.10 (3H, s), 1.95-1.80 (4H, m) 1.35 (3H, s).

Reference： [1]Current Patent Assignee: ONO PHARMACEUTICAL CO LTD - US5055598, 1991, A

50
[ 10210-17-0 ]
[ 38972-02-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With bromine In acetic acid at 20℃;	5.1 A solution of 4-(3-hydroxy-propyl)-phenol (10 g, 65.7 mmol) in glacial acetic acid (73.8 mL) was treated with a solution of bromine (7.4 mL, 144.5 mmol) in glacial acetic acid (7.3 mL). The reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum. The resulting residue was diluted with toluene (37 mL) and the solvent was again concentrated under vacuum. The resulting residue was dissolved in tetrahydrofuran (46 mL) and a 4N aqueous sodium hydroxide solution (64 mL) was added followed by water (27.5 mL). The reaction was stirred at room temperature for 2.5 h and the pH was adjusted to 5 by the addition of concentrated hydrochloric acid (14 mL). The layers were separated (the bottom layer is product). The aqueous layer was extracted with methyl tert-butyl ether (3 x 100 mL). The organic layers were combined, dried with sodium sulfate, filtered and concentrated under vacuum. The resulting residue was purified by column chromatography using silica gel eluted with a 1:1 ethyl acetate:hexanes solution. The desired fractions were collected and concentrated under vacuum. The resulting oil was dried under high vacuum overnight to afford 6-dibromo-4-(3-hydroxy-propyl)-phenol (20) (20.2 g, 99%) as a pink oil; LRMS for C9Hi0Br2O2 (M-H) m/z = 309. Molecular Weight =309.9869; Exact Mass =307.9048
	With bromine; acetic acid at 20℃;

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2007/9913, 2007, A1 Location in patent: Page/Page column 79-80
[2]Kelly, Martha J.; Pietranico-Cole, Sherrie; Larigan, J. Douglas; Haynes, Nancy-Ellen; Reynolds, Charles H.; Scott, Nathan; Vermeulen, John; Dvorozniak, Mark; Conde-Knape, Karin; Huang, Kuo-Sen; So, Sung-Sau; Thakkar, Kshitij; Qian, Yimin; Banner, Bruce; Mennona, Frank; Danzi, Sara; Klein, Irwin; Taub, Rebecca; Tilley, Jefferson [Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 3912 - 3923]

51
[ 10210-17-0 ]
[ 60456-23-7 ]
[ 1160754-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone for 18h; Reflux;	1 Step 1 5-[4-((R)-2,2-Dimethyl-[1,3]dioxolane-4-ylmethoxy)-phenyl]-pentane-1,2-diamine To 3-(4-hydroxyphenyl)-1-propanol (10 g, 66 mmol) and potassium carbonate (13.5 g, 100 mmol) in acetone (200 ml) is added (S)-glycidol (6.5 ml, 100 mmol). The mixture is heated at reflux for 18 hours. After cooling to room temperature the solvent is removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer is further extracted twice with EtOAc and the combined organic portions are washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography on silica eluding with 1:1 EtOAc/iso-hexane to afford (S)-3-[4-(3-Hydroxy-propyl)-phenoxy]-propane-1,2-diol as a white solid; 1H NMR (CDCl3): 1.20 (1H, br), 1.85 (2H, pent, J=6.8 Hz), 1.98 (1H, br), 2.58 (1H, br), 2.65 (2H, tr, J=6.9 Hz), 3.56 (2H, tr, J=6.8 Hz), 3.72 (1H, m), 3.83 (1H, m), 4.00 (2H, dd, J=2.1 Hz, J=6.5 Hz), 4.09 (1H, br), 6.82 (2H, d, J=7.4 Hz), 7.10 (2H, d, J=7.4 Hz).
	With potassium carbonate In acetone	2.1 5-14-((R)-2,2-Dimethyl-[1,3]dioxolane-4-ylmethoxy)-phenybenzoyl}-pentane-1,2-diamine To 3-(4-hydroxyphenyl)-1-propanol (10 g, 66 mmol) and potassium carbonate (13.5 g, 100 mmol) in acetone (200 ml) is added (S)-glycidol (6.5 ml, 100 mmol). The mixture is heated at reflux for 18 hours. After cooling to room temperature the solvent is removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer is further extracted twice with EtOAc and the combined organic portions are washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography on silica eluting with 1:1 EtOAc/iso-hexane to afford (S)-3-[4-(3-Hydroxy-propyl)-phenoxy]-propane-1,2-diol as a white solid; 1H NMR (CDCl3): 1.20 (1H, br), 1.85 (2H, pent, J=6.8 Hz), 1.98 (1H, br), 2.58 (1H, br), 2.65 (2H, tr, J=6.9 Hz), 3.56 (2H, tr, J=6.8 Hz), 3.72 (1H, m), 3.83 (1H, m), 4.00 (2H, dd, J=2.1 Hz, J=6.5 Hz), 4.09 (1H, br), 6.82 (2H, d, J=7.4 Hz), 7.10 (2H, d, J=7.4 Hz).
	With potassium carbonate In acetone for 18h; Reflux;	H.1 5-14-((R)-2,2-Dimethyl-[1,3]dioxolane-4-ylmethoxy)-phenybenzoyl}-pentane-1,2-diamine To 3-(4-hydroxyphenyl)-1-propanol (10 g, 66 mmol) and potassium carbonate (13.5 g, 100 mmol) in acetone (200 ml) is added (S)-glycidol (6.5 ml, 100 mmol). The mixture is heated at reflux for 18 hours. After cooling to room temperature the solvent is removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer is further extracted twice with EtOAc and the combined organic portions are washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography on silica eluting with 1:1 EtOAc/iso-hexane to afford (S)-3-[4-(3-Hydroxy-propyl)-phenoxy]-propane-1,2-diol as a white solid; 1H NMR (CDCl3): 1.20 (1H, br), 1.85 (2H, pent, J=6.8 Hz), 1.98 (1H, br), 2.58 (1H, br), 2.65 (2H, tr, J=6.9 Hz), 3.56 (2H, tr, J=6.8 Hz), 3.72 (1H, m), 3.83 (1H, m), 4.00 (2H, dd, J=2.1 Hz, J=6.5 Hz), 4.09 (1H, br), 6.82 (2H, d, J=7.4 Hz), 7.10 (2H, d, J=7.4 Hz).

With potassium carbonate In acetone for 18h; Reflux;

1 To 3-(4-hydroxyphenyl)-l-propanol (10.0 g, 66.0 mmol) and potassium carbonate (13.5 g, 100 mmol) in acetone (200 mL) is added (S)-glycidol (6.5 niL, 100 mmol). The mixture is heated at reflux for 18 h. After cooling to RT the solvent is removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer is further extracted twice with EtOAc and the combined organic portions are washed with water, brine, then dried (MgSθ4), filtered and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2, EtOAc:zso-hexane, 1:1) to afford the title compound as a white solid.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2010/130506, 2010, A1 Location in patent: Page/Page column 109
[2]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2011/98311, 2011, A1
[3]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2015/231142, 2015, A1 Location in patent: Paragraph 2478
[4]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2009/138378, 2009, A1 Location in patent: Page/Page column 44-45

52
[ 10210-17-0 ]
[ 78-93-3 ]
[ 851124-74-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With sodium hydroxide In tetrahydrofuran at 20 - 40℃; for 0.166667h; Stage #2: butanone In tetrahydrofuran at 0 - 40℃; for 0.5h; Stage #3: With chloroform at 0 - 40℃; for 26h;	27.1 To a stirred solution of 3- (4-hydroxyphenyl) propan-l-ol (9 g, 1 eq, 59.2 mmol) obtained in step 1 of Preparation 16 in 296 mL of dry THF, powdered NaOH (21.6 g, 9 eq, 532.8 mmol) was added and was stirred at 20-40 °C for 10 min. Then methyl ethyl ketone (52 mL, 10 eq, 592 mmol) was added at 20-40 °C and followed by stirring at 0 °C for 30 min. Then CHC13 (19 mL, 4 eq, 236.8 mmol) was added drop wise at 0 °C with vigorous stirring. After the addition of CHC13 reaction temperature was maintained at 0 °C for 2 h after which it was allowed to attain 20-40 ° C while vigorous stirring for 24 h. Being guided by TLC, reaction was stopped. Reaction mixture was acidified with 4N HC1 and extracted with ethyl acetate (200 mL x2) 0rganic layer was dried (Na2SO4), condensed, and the residue was chromatographed using ethyl acetate and hexane to obtain the title compound as thick mass (6.4 g, 43 % yield). In this step compound was bit impure, and was characterized in the next step.

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2005/40102, 2005, A2 Location in patent: Page/Page column 68

53
[ 10210-17-0 ]
[ 58479-61-1 ]
[ 400838-08-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Han, Jae Hyun; Kwon, Young Eun; Sohn, Jeong-Hun; Ryu, Do Hyun [Tetrahedron, 2010, vol. 66, # 9, p. 1673 - 1677]

54
[ 10210-17-0 ]
[ 541-41-3 ]
carbonic acid ethyl ester 4-(3-hydroxy-propyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In acetonitrile at -80 - 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Barattin, Régis; Perrotton, Thomas; Trompier, Doriane; Lorendeau, Doriane; Pietro, Attilio Di; D'Hardemare, Amaury Du Moulinet; Baubichon-Cortay, Hélne [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6265 - 6274]

55
[ 40807-61-2 ]
[ 10210-17-0 ]
[ 1295644-41-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With trifluorormethanesulfonic acid In nitrobenzene at 0 - 20℃;	Intermediate 94-(3-Hydroxy-propyl)-2-(4-phen l-piperidin-4-yl)-phenolTo a solution of 4-phenylpiperidin-4-ol (5 g, 28.2 mmol) and 3-(4-hydroxyphenyl)-l- propanol (12.9 g, 84.6 mmol) in nitrobenzene (25 mL) at 0 °C was added dropwise triflic acid (7.5 mL, 84.6 mmol). The reaction mixture was stirred at RT for 48 h, poured onto ice, basified to pH 9 by the addition of 25% aqueous sodium hydroxide then extracted with EtOAc (3 x 80 mL). The combined organic layers were washed with water, brine, dried (MgS04), filtered, evaporated and purified on SCX-2 cartridge (eluting with MeOH then 2 M NH3 in MeOH) to give the title compound (5.5 g, 63 %).LCMS (Method 1): Rt 2.59 min, m/z 312 [M+H]

Reference： [1]Current Patent Assignee: PULMAGEN THERAPEUTICS LLP; CHARLES RIVER LABORATORIES INTERNATIONAL INC; ASTRAZENECA PLC - WO2011/48409, 2011, A1 Location in patent: Page/Page column 41

56
[ 1120-90-7 ]
[ 10210-17-0 ]
3-(4-(pyridin-3-yloxy)phenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 21h; Inert atmosphere; chemoselective reaction;

Reference： [1]Maiti, Debabrata [Chemical Communications, 2011, vol. 47, # 29, p. 8340 - 8342]

57
[ 615-37-2 ]
[ 10210-17-0 ]
3-(4-(o-tolyloxy)phenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 120℃; for 21h; Inert atmosphere; chemoselective reaction;

Reference： [1]Maiti, Debabrata [Chemical Communications, 2011, vol. 47, # 29, p. 8340 - 8342]

58
[ 10210-17-0 ]
[ 90708-66-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sulfur trioxide pyridine complex; triethylamine In dimethyl sulfoxide at 20℃; for 1h;	4-hydroxyphenylpropionaldehyde was prepared by a synthesis analogous to that for 4-hydroxyphenylacetalde- hyde (Heterocycles, 2000, 53, 777-784). 3-(4-Hydroxyphe- nyl)-1-propanol (1.0 g, 6.6 mmol, Aldrich) was dissolved in dimethylsulfoxide (8 mE, Aldrich). TEA (2.0 mE, 14 mmol, Aldrich) was added slowly with stirring. Pyridine-sulthr trioxide (503.py) complex (2.3 g, 15 mmol, Aldrich) was completely dissolved in dimethylsulfoxide (9 mE, Aldrich) and this solution was added drop-wise to the alcohol, with vigorous stirring. Afier stirring for 1 h at room temperature, the reaction was diluted with CH2C12, then washed with ice-cold water. The organic layer was dried over Na2504, filtered, and concentrated to dryness. Purification using silica gel chromatography with hexane-ethyl acetate as eluent (5:1, then 2:1) yielded 745 mg (75%) of 4-hydroxyphenylpropionaldehyde.
745 mg (75%)	With triethanolamine In dimethyl sulfoxide	1.B.R B) 3-(4-Hydroxyphenyl)-1-propanol (1.0 g, 6.6 mmol, Aldrich) was dissolved in dimethylsulfoxide (8 mL, Aldrich). TEA (2.0 mL, 14 mmol, Aldrich) was added slowly with stirring. Pyridine-sulfur trioxide (SO3.py) complex (2.3 g, 15 mmol, Aldrich) was completely dissolved in dimethylsulfoxide (9 mL, Aldrich) and this solution was added drop-wise to the alcohol, with vigorous stirring. After stirring for 1 h at room temperature, the reaction was diluted with CH2Cl2, then washed with ice-cold water. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness. Purification using silica gel chromatography with hexane-ethyl acetate as eluent (5:1, then 2:1) yielded 745 mg (75%) of 4-hydroxyphenylpropionaldehyde.

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC. - US2015/132259, 2015, A1 Location in patent: Paragraph 0574
[2]Current Patent Assignee: BIOGEN IDEC INC. - US8017733, 2011, B2

59
[ 501-97-3 ]
[ 10210-17-0 ]
[ 1379072-68-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 23%	With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;

Reference： [1]Szostak, Michal; Spain, Malcolm; Procter, David J. [Organic Letters, 2012, vol. 14, # 3, p. 840 - 843]

60
[ 1397255-01-4 ]
[ 10210-17-0 ]
[ 2785-89-9 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; ammonium formate;palladium 10% on activated carbon; In water; ethyl acetate; at 80℃; for 3h;	Example 20: Generating 4-ethyl-2-methoxyphenol and 4-(3-hydroxypropyl)phenol from 3-(4-(2-(4-hydroxy-3-methoxyphenyl)-2-oxoethoxy)phenyl)acrylaldehyde.Pd/C (10 mol%) is weighed into a reaction flask. A solvent mixture consisting of ethyl acetate and water (4: 1) and ammonium formate (2 equivalents) is added, the reaction flask is capped with a rubber septa and the mixture is heated (80 C) for 2 minutes. Substrate 3-(4-(2-(4-hydroxy-3-methoxyphenyl)-2-oxoethoxy)phenyl)- acrylaldehyde is added. The reaction is run for 120 minutes and then 3 equivalents of formic acid are added and the reaction is run at 80 C for 1 hour and the reaction is quenched with brine. The product is extracted by DCM and the organic phase is dried by Na2S04. The products were purified by silica column to yield the products in above 90% yield.

Reference： [1]Patent: WO2012/121659,2012,A1 .Location in patent: Page/Page column 14

61
[ 1397255-02-5 ]
[ 23795-02-0 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; ammonium formate;palladium 10% on activated carbon; In water; ethyl acetate; at 80℃; for 3h;	Example 22: Generating ethyl 3-(4-hydroxyphenyl)propanoate and and 4-(3- hydroxypropyl)phenol from ethyl 3-(4-(2-(4-hydroxy-3-methoxyphenyl)-2- oxoethoxy)phenyl) acrylate .Pd/C (10 mol%) is weighed into a reaction flask. A solvent mixture consisting of ethyl acetate and water (4: 1) and ammonium formate (2 equivalents) is added, the reaction flask is capped with a rubber septa and the mixture is heated (80 C) for 2 minutes. Substrate ethyl 3-(4-(2-(4-hydroxy-3-methoxyphenyl)-2- oxoethoxy)phenyl)acrylate is added. The reaction is run for 120 minutes and then 3 equivalents of formic acid are added and the reaction is run at 80 C for 1 hour and the reaction is quenched with brine. The product is extracted by DCM and the organic phase is dried by Na2S04. The products were purified by silica column to yield the products in above 90% yield.

Reference： [1]Patent: WO2012/121659,2012,A1 .Location in patent: Page/Page column 15

62
[ 10210-17-0 ]
[ 46118-02-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With carbonic acid dimethyl ester at 20℃; for 1h; Stage #2: With sodium dithionite In water at 20℃; for 0.0833333h; chemoselective reaction;

Reference： [1]Location in patent: experimental part Bernini, Roberta; Crisante, Fernanda; Barontini, Maurizio; Tofani, Daniela; Balducci, Valentina; Gambacorta, Augusto [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 30, p. 7408 - 7416]

63
[ 10210-17-0 ]
[ 2902-69-4 ]
4-hydroxy-benzenepropanol-α-benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With N,N,N',N'',N'''-pentamethyldiethylenetriamine In acetonitrile at 20 - 25℃; for 12h;	4.5. PMDETA-catalyzed selective benzoylation of phenolic alcohols with trichloromethyl phenyl ketone (1) General procedure: General procedure: Trichloromethyl phenyl ketone (0.447 g, 2 mmol), phenolic alcohol (2 mmol), and PMDETA (0.007 g, 0.04 mmol; 0.035 g, 0.2 mmol in case of entries 4-6) were taken in a 25 mL round bottom flask. To this heterogeneous mixture, acetonitrile (1 mL) was added, the flask was stoppered and the resulting viscous solution was stirred at room temperature (20-25 °C) on a magnetic stirrer. The progress of the reaction was monitored by TLC. After the completion of the reaction (12-60 h), the crude reaction mixture was purified by flash column chromatography using n-hexane/EtOAc (7:3 v/v) as the solvent for elution to provide the phenolic alkyl benzoates 4a-k in 84-95% yields. The products 4a,26b 4b,38 4c,20a 4i,12 4j,39 4k,40 and 5b41 are known in the literature.

Reference： [1]Ram, Ram N.; Soni, Vineet Kumar; Gupta, Dharmendra Kumar [Tetrahedron, 2012, vol. 68, # 44, p. 9068 - 9075]

64
[ 10210-17-0 ]
[ 618-40-6 ]
[ 1415425-73-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With but-2-enenitrile; dodecacarbonyl-triangulo-triruthenium; 2,2'-bis(diphenylphosphino)biphenyl; zinc(II) chloride In tert-Amyl alcohol at 130℃; for 3h; Inert atmosphere; Microwave irradiation;

Reference： [1]Porcheddu, Andrea; Mura, Manuel G.; De Luca, Lidia; Pizzetti, Marianna; Taddei, Maurizio [Organic Letters, 2012, vol. 14, # 23, p. 6112 - 6115]

65
[ 10210-17-0 ]
[ 1315377-15-1 ]
[ 1315377-16-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With caesium carbonate In acetonitrile at 0℃; for 1h; Inert atmosphere; Stage #2: 2-(4-((E)-2-((E)-3-((E)-2-(1-(4-bromobenzyl)-3,3-dimethylindolin-2-ylidene)ethylidene)-5-tert-butyl-2-chlorocyclohex-1-enyl)vinyl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile In acetonitrile at 20℃; for 4h;	Synthesis of the Chromophore 13 Synthesis of the Chromophore 13 [0260] A solution of 700 mg (2.16 mmol) of cesium carbonate in 15 mL of anhydrous acetonitrile is prepared and cooled to 0° C. in a two-necked flask flamed under vacuum and purged with argon. A solution of 250 mg (1.66 mmol) of 4-(3-hydroxypropyl)phenol in 5 mL of anhydrous acetonitrile is then added dropwise. After 1 h and after returning to room temperature, a solution of 1.0 g (1.36 mmol) of compound 12 in 10 mL of anhydrous acetonitrile is added and the solution is stirred for 4 h. The solution is neutralized, stopped by the addition of 5 mL of a dilute HCl solution. The solution is extracted with 3 times 20 mL of dichloromethane. The organic phases are combined, dried over MgSO4, filtered and evaporated. The crude product is purified by column chromatography (SiO2, CH2Cl2/EtOAc: 9/1, v/v). [0261] Mass: 810 mg (70%), green-blue solid. [0262] 1H NMR (500 MHz, CDCl3): δ 1.11 (s, 9H, CH3), 1.28 (s, 6H, CH3), 1.42 (s, 6H, CH3), 1.55 (m, 1H, CH), 1.78 (m, 2H, CH2), 1.95 (m, 1H, ring CH2), 2.14 (m, 1H, ring CH2), 2.65 (m, 4H, ring CH2, CH2), 3.65 (m, 2H, CH2OH), 4.88 (m, 2H, NCH2), 5.48 (d, 1H, J=13.3 Hz), 6.25 (d, 1H, J=15.4 Hz), 6.83 (d, 1H, J=7.9 Hz), 6.87 (d, 2H, CHar, J=8.2 Hz), 7.01 (t, 1H, J=7.5 Hz, J=7.4 Hz), 7.08 (d, 2H, J=7.9 Hz), 7.13 (d, 2H, J=8.1 Hz), 7.19 (m, 2H), 7.38 (d, 1H, J=13.2 Hz), 7.45 (d, 2H, CHar, J=8.0), 7.64 (d, 1H, J=15.3 Hz). [0263] 13C NMR (125 MHz, CDCl3): δ 25.1, 25.5, 26.8, 26.8, 27.5, 28.1, 28.2, 31.2, 32.5, 34.4, 42.9, 46.5, 47.1, 62.0, 94.5, 96.0, 96.5, 107.8, 109.9, 111.7, 112.6, 113.5, 114.5, 115.5, 121.8, 122.1, 122.4, 122.5, 122.9, 128.2, 128.3, 129.9, 132.2, 133.1, 134.6, 135.7, 139.5, 142.4, 143.6, 157.8, 161.0, 164.0, 173.3, 176.3. [0264] λmax (CH2Cl2): 792 nm.

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF LYON - US2013/123508, 2013, A1 Location in patent: Paragraph 0259-0264

66
[ 10210-17-0 ]
[ 1315377-13-9 ]
[ 1315377-23-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With caesium carbonate In acetonitrile at 0℃; for 1h; Inert atmosphere; Stage #2: 6-((E)-2-((E)-2-(5-tert-butyl-2-chloro-3-((E)-2-(4-cyano-5-(dicyanomethylene)-2,2-dimethyl-2,5-dihydrofuran-3-yl)vinyl)cyclohex-2-enylidene)ethylidene)-3,3-dimethylindolin-1-yl)-N-(4-((trimethylsilyl)ethynyl)phenyl)hexanamide In acetonitrile at 20℃; for 8h;	Synthesis of the Chromophore 27 Synthesis of the Chromophore 27 [0275] A solution of 110 mg (0.34 mmol) of cesium carbonate in 8 mL of anhydrous acetonitrile is prepared and cooled to 0° C. in a two-necked flask flamed under vacuum and purged with argon. A solution of 40 mg (0.26 mmol) of 4-(3-hydroxypropyl)phenol in 1 mL of anhydrous acetonitrile is then added dropwise. After 1 h and after returning to room temperature, a solution of 183 mg (0.22 mmol) of compound 10 in 10 mL of anhydrous acetonitrile is added and the solution is stirred for 8 h. The solution is neutralized, stopped by the addition of 5 mL of a dilute HCl solution. The solution is extracted with 3 times 20 mL of dichloromethane. The organic phases are combined, dried over MgSO4, filtered and evaporated. The crude product is purified by column chromatography (SiO2, CH2Cl2/EtOAc: 9/1, v/v). [0276] Mass: 810 mg (70%), green-blue solid. [0277] 1H NMR (500 MHz, CD2Cl2): δ 0.25 (s, 9H), 1.09 (s, 9H), 1.27 (m, 6H), 1.46 (s, 8H), 1.67 (m, 1H), 1.76 (m, 6H), 2.19 (m, 2H), 2.34 (t, 2H, J=8.5 Hz, J=15.1 Hz), 2.63 (t, 2H, J=6.3 Hz, J=14.6 Hz), 2.78 (d, 1H, J=18.6 Hz), 2.87 (d, 1H, J=18.8 Hz), 3.56 (m, 2H), 3.80 (m, 2H), 5.69 (d, 1H, J=12.5 Hz), 6.19 (d, 1H, J=16.2 Hz), 6.86 (d, 1H, J=10.0 Hz), 6.94 (d, 2H, J=6.3 Hz), 7.03 (t, 1H), 7.17 (m, 4H), 7.24 (t, 1H, J=6.3 Hz, J=12.5 Hz), 7.31 (s, 1H), 7.41 (d, 2H, J=8.7 Hz), 7.48 (d, 2H, J=8.7 Hz), 7.57 (d, 1H, J=13.7 Hz), 7.80 (d, 1H, J=14.9 Hz). [0278] 13C NMR (125 MHz, CD2Cl2): δ -0.26, 24.9, 25.2, 25.5, 26.4, 26.6, 26.7, 27.4, 27.7, 27.9, 31.2, 32.4, 34.6, 37.2, 43.2, 47.5, 61.8, 93.5, 95.5, 96.1, 104.6, 108.4, 112.3, 113.1, 113.7, 114.7, 118.5, 119.1, 121.9, 122.1, 122.3, 122.6, 128.4, 130.1, 132.8, 134.9, 135.8, 138.4, 140.1, 142.4, 143.4, 158.1, 161.8, 166.1, 170.9, 172.6, 176.8. [0279] λmax (CH2Cl2): 818 nm.

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF LYON - US2013/123508, 2013, A1 Location in patent: Paragraph 0275-0279

67
[ 10210-17-0 ]
[ 1315377-19-5 ]
[ 1315377-22-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With caesium carbonate In acetonitrile at 0℃; for 1h; Inert atmosphere; Stage #2: N-(4-azidophenyl)-6-((E)-2-((E)-2-(5-tert-butyl-2-chloro-3-((E)-2-(4-cyano-5-(dicyanomethylene)-2,2-dimethyl-2,5-dihydrofuran-3-yl)vinyl)cyclohex-2-enylidene)ethylidene)-3,3-dimethylindolin-1-yl)hexanamide In acetonitrile at 20℃; for 4h;	Synthesis of the Chromophore 25 Synthesis of the Chromophore 25 [0270] A solution of 163 mg (0.49 mmol) of cesium carbonate in 8 mL of anhydrous acetonitrile is prepared and cooled to 0° C. in a two-necked flask flamed under vacuum and purged with argon. A solution of 59 mg (0.38 mmol) of 4-(3-hydroxypropyl)phenol in 3 mL of anhydrous acetonitrile is then added dropwise. After 1 h and after returning to room temperature, a solution of 250 mg (0.32 mmol) of compound 23 in 10 mL of anhydrous acetonitrile is added and the solution is stirred for 4 h. The solution is neutralized, stopped by the addition of 5 mL of a dilute HCl solution. The solution is extracted with 3 times 20 mL of dichloromethane. The organic phases are combined, dried over MgSO4, filtered and evaporated. The crude product is purified by column chromatography (SiO2, CH2Cl2/EtOAc: 9/1, v/v). [0271] Mass: 810 mg (70%), green solid. [0272] 1H NMR (500 MHz, CD2Cl2): δ 1.12 (s, 9H), 1.30 (m, 6H), 1.47 (s, 8H), 1.68 (m, 1H), 1.80 (m, 6H), 2.20 (m, 2H), 2.36 (m, 2H), 2.56 (m, 2H), 2.80 (d, 1H, J=20.0 Hz), 2.90 (d, 1H, J=20.0 Hz), 3.59 (m, 2H), 3.82 (m, 2H), 5.70 (d, 1H, J=13.0 Hz), 6.22 (d, 1H, J=16.0 Hz), 6.86 (d, 1H, J=7.8 Hz), 6.98 (m, 4H), 7.28 (m, 2H), 7.17 (m, 5H), 7.54 (m, 3H), 7.80 (m, 1H). [0273] 13C NMR (125 MHz, CD2Cl2): δ 24.9, 25.2, 25.5, 26.5, 26.6, 26.7, 27.2, 27.7, 27.8, 31.1, 32.5, 34.5, 37.2, 43.1, 43.2, 47.5, 61.8, 95.3, 96.2, 100.0, 108.4, 112.4, 113.2, 113.8, 114.5, 115.1, 119.4, 121.2, 122.3, 128.2, 129.5, 130.3, 133.1, 134.6, 135.3, 136.2, 140.1, 141.9, 143.2, 158.1, 162.0, 165.9, 170.4, 172.5, 176.6. [0274] λmax (CH2Cl2): 818 nm.

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF LYON - US2013/123508, 2013, A1 Location in patent: Paragraph 0270-0274

68
[ 108-05-4 ]
[ 10210-17-0 ]
C₁₀H₁₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With rubidium fluoride In acetonitrile at 80℃; for 0.5h;

Reference： [1]Miyazawa, Toshifumi; Yamamoto, Masato; Danjo, Hiroshi [Monatshefte fur Chemie, 2013, vol. 144, # 9, p. 1351 - 1354]

69
[ 10210-17-0 ]
[ 5750-76-5 ]
3-(4-((2,5-dichloropyrimidin-4-yl)oxy)phenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; regioselective reaction;	5.1.2. General procedure for the preparation of 5a-d General procedure: Potassium carbonate (2.42 g, 17.5 mmol) and 2,4,5-trichloropyrimidine (1.0 mL, 8.72 mmol) were added to the solution of 4a-d (8.72 mmol) in DMF (20 mL). The mixture was stirred at room temperature for 2 h. The reaction mixture was poured into ice water and white solid was precipitated. After filtration, filter cake was dried and was used for further steps without purification.

Reference： [1]Han, Chun; Huang, Zhangjian; Zheng, Chao; Wan, Ledong; Lai, Yisheng; Peng, Sixun; Ding, Ke; Ji, Hongbin; Zhang, Yihua [European Journal of Medicinal Chemistry, 2013, vol. 66, p. 82 - 90]

70
[ 2979-06-8 ]
[ 10210-17-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 82 - 90

71
[ 3690-05-9 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12h;	5.1.1. 4-(3-Hydroxypropyl)phenol (4a) Compound 3 [27] (1 g, 6.7 mmol) was stirred under H2 in thepresence of 10% palladium carbon (catalytic amount) in MeOH for 12 h. The mixture was filtered through a pad of Celite, the filtrate was dried and concentrated to offer 4a as a white solid (0.99 g, 98%yield, m.p. 52-53oC); Analytical data for 4a: 1H NMR (500 MHz,CDCl3): d 1.83e1.89 (m, 2H), 2.63 (t, J 7.8 Hz, 2H), 3.01 (brs, 1H),3.67 (t, J 6.5 Hz, 2H), 6.74 (d, J 8.4 Hz, 2H), 7.05 (d, J 8.3 Hz,2H); 13C NMR (75 MHz, CDCl3): d 155.68, 136.7,129.94, 111.37, 62.06, 33.87, 31.48; ESI-MS: m/z 151.1 [M-H]-; ESI-HRMS (m/z):[M-H]- calcd for C9H12O2 151.0765; obsd 151.0766.

Reference： [1]Han, Chun; Huang, Zhangjian; Zheng, Chao; Wan, Ledong; Lai, Yisheng; Peng, Sixun; Ding, Ke; Ji, Hongbin; Zhang, Yihua [European Journal of Medicinal Chemistry, 2013, vol. 66, p. 82 - 90]

72
[ 24424-99-5 ]
[ 10210-17-0 ]
[ 1559067-01-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 18-crown-6 ether; potassium carbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	A Synthesis of 3-(4-t-butoxycarbonyl)phenyl-l-propanol (1): To a 250mL round bottom flask was added 3-(4-hydroxyphenyl)-l-propanol (lOg, 65.7 mmol), dichloromethane (75 mL) and di-ieri-butyldicarbonate (14.36g, 65.7mmol). The mixture was stirred under nitrogen and cooled to 0°C in an ice bath. Potassium carbonate (24.37g, 176 mmol) and 18-crown-6 (0.90g, 3.4mmol) dissolved in dichloromethane were added. The resulting mixture was stirred and warmed to room temperature overnight. The crude reaction mixture was filtered through a silica gel and rinsed with ethyl acetate. The resulting solvent was evaporated and the residue was purified via flash column chromatography on silica gel with ethyl acetate: hexane (40%) as eluant. The third fraction was combined and the solvent removed to give 15.7g (yield: 95%) of 1 as a yellow oil. The product was characterized by XH NMR and MS.
95%	With 18-crown-6 ether; potassium carbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	A Synthesis of 3-(4-i-butoxycarbonyl)phenyl-l-propanol (7): To a 250mL round bottom flask was added 3-(4-hydroxyphenyl)-l-propanol (lOg, 65.7 mmol), dichloromethane (75 mL) and di-ieri-butyldicarbonate (14.36g, 65.7mmol). The mixture was stirred under nitrogen and cooled to 0°C in an ice bath. Potassium carbonate (24.37g, 176 mmol) and 18-crown-6 (0.90g, 3.4mmol) dissolved in dichloromethane were added. The resulting mixture was stirred and warmed to room temperature overnight. The crude reaction mixture was filtered through a silica gel and rinsed with ethyl acetate. The resulting solvent was evaporated and the residue was purified via flash column chromatography on silica gel with ethyl acetate: hexane (40%) as eluant. The third fraction was combined and the solvent removed to give 15.7g (yield: 95%) of 1 as a yellow oil. The product was characterized by lW NMR and MS.

Reference： [1]Current Patent Assignee: IRRESISTIBLE MATERIALS - WO2014/78097, 2014, A1 Location in patent: Page/Page column 21
[2]Current Patent Assignee: IRRESISTIBLE MATERIALS - WO2014/137663, 2014, A1 Location in patent: Page/Page column 21

73
[ 10210-17-0 ]
[ 18162-48-6 ]
[ 215776-67-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil for 1h;	MM-1-28 (MM-1-28) An oven dried 50 mL round bottom flask equipped with stir bar was charged with NaH (80 mg, 60% dispersion in mineral oil) . THF (5 mL) was added, and the mixture cooled to 0 °C. 4- (3- Hydroxypropyl) phenol (300 mg, 1.97 mmol) was added dropwise as a solution in THF (4 mL + 1 mL rinse) . After effervescence ceased, the mixture was warmed to room temperature, and an additional 5 mL THF was added. After 1 hour at room temperature, TBSC1 (312 mg, 2.'07 mmol, 1.05 equiv) was added, and the mixture was allowed to stir for an additional hour, whereupon the mixture was diluted with Et20 (15 mL) . The ethereal phase was washed with sat. NH4C1 (10 mL) and H20 (5 mL) . The aqueous phase was extracted with Et20 (3 x 15 mL) , and the combined extracts were dried over sat. aqueous NaCl (10 mL) , Na2S04, decanted and concentrated. Flash chromatography (Si02, 30% EtOAc/hexanes) gave 377 mg (72%) of the silyl ether. 1ti NMR (300 MHz , CDC13) δ 7.05 (s, J = 8.4 Hz, 2H) , 6.77 (d, J = 8.4 Hz, 2H) , 3.67 (m, 2H) , 2.64 (dd, J = 8.5, 6.8 Hz, 2H) , 1.95 - 1.79 (m, 2H) , 0.99 (s, 9H) , 0.20 (s, 6H) .
72%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH - WO2014/131023, 2014, A1 Location in patent: Page/Page column 130
[2]Morin, Matthew D.; Wang, Ying; Jones, Brian T.; Su, Lijing; Surakattula, Murali M. R. P.; Berger, Michael; Huang, Hua; Beutler, Elliot K.; Zhang, Hong; Beutler, Bruce; Boger, Dale L. [Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4812 - 4830]

74
[ 10210-17-0 ]
[ 990-91-0 ]
3-[4-(dibenzyl)phosphoryloxy]phenyl-1-propanol [ No CAS ]
3-(4-hydroxyphenyl)-1-propyl dibenzyl phosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) tetrabutoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Inert atmosphere; Overall yield = 84 %; chemoselective reaction;	General procedure for the phosphorylation of diols. General procedure: The diol (0.49 mmol) was dissolved in 1.0 mL of CH2Cl2. N,N-Diisopropylethylamine (0.130 mL, 0.746 mmol) was added to the solution, followed by tetrabenzylpyrophosphate (0.320 g, 0.594 mmol). Ti(OtBu)4 (19 μL, 0.049 mmol, 10 mol %) was added and the reaction was stirred for 4 h at room temperature. To quench the reaction, the crude solution was filtered through a 5 mL plastic syringe containing 2 mL of 20:1 Silica/MgSO4 and washed with 60 mL of 75% EtOAc/hexanes. The filtrate was concentrated under reduced pressure. The crude product was purified using silica gel chromatography.

Reference： [1]Coppola, Kyle A.; Testa, Joseph W.; Allen, Emily E.; Sculimbrene, Bianca R. [Tetrahedron Letters, 2014, vol. 55, # 30, p. 4203 - 4206]

75
[ 10210-17-0 ]
[ 990-91-0 ]
3-(4-hydroxyphenyl)-1-propyl dibenzyl phosphate [ No CAS ]
C₃₇H₃₈O₈P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) tetrabutoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Inert atmosphere; Overall yield = 84 %;	General Procedure for the Phosphorylation of Diols General procedure: The diol (0.49 mmol) was dissolved in1.0 mL of CH2Cl2. N,N-Diisopropylethylamine (0.130 mL, 0.746 mmol) was added to thesolution, followed by tetrabenzylpyrophosphate (0.320 g, 0.594 mmol;). Ti(OtBu)4 (19 μL,0.049 mmol, 10 mol %) was added and the reaction was stirred for 4 h at room temperature. Toquench the reaction, the crude solution was filtered through a 5 mL plastic syringe containing 2mL of 20:1 Silica/MgSO4 and washed with 60 mL of 75% EtOAc/hexanes. The filtrate wasconcentrated under reduced pressure. The crude product was purified using silica gelchromatography.

Reference： [1]Coppola, Kyle A.; Testa, Joseph W.; Allen, Emily E.; Sculimbrene, Bianca R. [Tetrahedron Letters, 2014, vol. 55, # 30, p. 4203 - 4206]

76
[ 1135-24-6 ]
[ 10210-17-0 ]
(E)-3-(4-hydroxyphenyl)propyl 3-(4-hydroxy-3-methoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; chemoselective reaction;	4.3.1. Preparation of analogs 5-9 and 13-47 by chemoselective Mitsunobu esterification General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 °C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 °C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

Reference： [1]Mohyeldin, Mohamed M.; Busnena, Belnaser A.; Akl, Mohamed R.; Dragoi, Ana Maria; Cardelli, James A.; El Sayed, Khalid A. [European Journal of Medicinal Chemistry, 2016, vol. 118, p. 299 - 315]

77
[ 10210-17-0 ]
[ 530-59-6 ]
(E)-3-(4-hydroxyphenyl)propyl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; chemoselective reaction;	4.3.1. Preparation of analogs 5-9 and 13-47 by chemoselective Mitsunobu esterification General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 °C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 °C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

Reference： [1]Mohyeldin, Mohamed M.; Busnena, Belnaser A.; Akl, Mohamed R.; Dragoi, Ana Maria; Cardelli, James A.; El Sayed, Khalid A. [European Journal of Medicinal Chemistry, 2016, vol. 118, p. 299 - 315]

78
[ 10210-17-0 ]
[ 104274-20-6 ]
(E)-3-(4-hydroxyphenyl)propyl3-(4-amino-3-methoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; chemoselective reaction;	4.3.1. Preparation of analogs 5-9 and 13-47 by chemoselective Mitsunobu esterification General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 °C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 °C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

Reference： [1]Mohyeldin, Mohamed M.; Busnena, Belnaser A.; Akl, Mohamed R.; Dragoi, Ana Maria; Cardelli, James A.; El Sayed, Khalid A. [European Journal of Medicinal Chemistry, 2016, vol. 118, p. 299 - 315]

79
[ 10210-17-0 ]
[ 104274-20-6 ]
(Z)-3-(4-hydroxyphenyl)propyl 3-(4-amino-3-methoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; chemoselective reaction;	4.3.1. Preparation of analogs 5-9 and 13-47 by chemoselective Mitsunobu esterification General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 °C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 °C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

Reference： [1]Mohyeldin, Mohamed M.; Busnena, Belnaser A.; Akl, Mohamed R.; Dragoi, Ana Maria; Cardelli, James A.; El Sayed, Khalid A. [European Journal of Medicinal Chemistry, 2016, vol. 118, p. 299 - 315]

80
[ 10210-17-0 ]
[ 108-24-7 ]
[ 25823-43-2 ]
[ 107866-55-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 17%	With dmap; triethylamine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere;	4-(3-Hydroxypropyl)phenyl acetate (35a) To asolution of diol 34 (2.43 g, 16.0 mmol) in CH2Cl2(20 mL) were added DMAP (590.3 mg, 4.79 mmol, 0.3 equiv) and Et3N(1.2 mL, 7.98 mmol, 0.5 equiv). The mixture was cooled to 0 °C and aceticanhydride (750 µL, 7.98 mmol, 0.5 equiv) was added dropwise. The reactionmixture was stirred at 0 °C for 5 min before being quenched with 50 mL of H2Oand extracted with CH2Cl2 (3x50 mL). The combined organic layers were washed with brine, dried with anhydrousNa2SO4 and concentrated in vacuo.Purification of the crude residue by column chromatography (20% EtOAc/hexanes)yielded 35a as a colorless oil (1.86 g, 60%) along with bisacetylated product(650.7 mg, 17%): Rf = 0.57 (40% EtOAc/hexanes); 1H NMR (300MHz, CDCl3) δ 7.17 (d, J= 8.4 Hz, 2H), 6.97 (d, J = 8.4 Hz, 2H), 3.61 (t, J = 6.6 Hz,2H), 2.66 (t, J = 6.6 Hz, 2H), 2.26 (s, 3H), 1.84 (quintet, J =6.6 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 169.9, 148.7,139.5, 129.4, 121.4, 61.9, 34.1, 31.4, 21.1; IR (thin film) 3342, 2939, 1755,1508, 1371, 1219 cm-1; HRMS (ESI) m/z calcd for C11H14NaO3(M + Na)+ 217.0841, found 217.0841.

Reference： [1]Kantee, Kawalee; Rukachaisirikul, Vatcharin; Tadpetch, Kwanruthai [Tetrahedron Letters, 2016, vol. 57, # 31, p. 3505 - 3509]

81
[ 20649-40-5 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃; for 6h;	3 Synthesis Example 3: Synthesis of 3- (4-hydroxyphenyl) propan-1-ol (SHHPA) (Compound 10b) 1.0 g (6.7 mmol) of 4-hydroxycinnamyl alcohol (Compound 9) synthesized in Synthesis Example 2 was dissolved in 50 mL of ethyl acetate (manufactured by Wako Pure Chemical Industries, Ltd.), placed in a pressure resistant container, and 5% palladium carbon 2.85 G (corresponding to 0.67 mmol, manufactured by N. E. Chemcat Co., Ltd.) was added, the mixture was pressurized to a hydrogen pressure of 0.3 Mpa and stirred at room temperature for 6 hours. After depressurization, palladium carbon was filtered and concentrated to obtain 0.49 g (yield 48%) of the objective 3- (4-hydroxyphenyl) propan-1-ol (SHHPA) (Compound 10b)

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP.; DAINIPPON KASEI - JP2016/132639, 2016, A Location in patent: Paragraph 0086; 0087

82
[ 10210-17-0 ]
2,6-diiodo-4-(3-hydroxypropyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sulfuric acid; dihydrogen peroxide; potassium iodide In methanol; water at 0 - 20℃; for 14h; Inert atmosphere;

Reference： [1]Ohishi, Yuki; Abe, Hajime; Inouye, Masahiko [European Journal of Organic Chemistry, 2017, vol. 2017, # 46, p. 6975 - 6979]

83
[3-(3-chloropropoxy)phenyl]dimethylamine [ No CAS ]
[ 10210-17-0 ]
3-(4-{3-[3-(dimethylamino)phenoxy]propoxy}phenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With 18-crown-6 ether; potassium carbonate In acetone for 48h; Reflux; Inert atmosphere;	2.1.1. 3-(4-{3-[3-(Dimethylamino)phenoxy]propoxy}phenyl)propan-1-ol (3) 3-(4-Hydroxyphenyl)-1-propanol (1 g, 6.58 mmol), dried K2CO3 (0.9 g, 6.58 mmol), 18-crown-6(0.173 g, 0.658 mmol) and [3-(3-chloropropoxy)phenyl]dimethylamine1 (1.4 g, 6.58 mmol)in acetone (50 mL) were heated at reflux and stirred vigorously under nitrogen for 48 h. Thevolatile materials were removed under reduced pressure and the residue was treated with100 mL CHCl3 and 50 mL H2O. The separated water was extracted three times with 100 mLCHCl3. The combined organic phases were dried with MgSO4 and the crude product waspurified by aluminum oxide column chromatography with CHCl3 as solvent. Yield: 0.712 g(33%). IR (ATR), ν/cm-1: 3372 (O-H), 3031 (Ar-H), 2933-2875 (Aliph. C-H), 1610, 1574, 1509,1471, 1450, 1353, 1235, 1175, 1150, 1058, 1012, 953, 825, 750, 686. 1H-NMR (400 MHz, CDCl3),(δ:ppm): 7.18-7.12 (m, 3H, Ar-H), 6.88 (d, 2H, J = 8.4, Ar-H), 6.40 (d, 1H, J = 8.1, Ar-H), 6.35(d, 2H, J = 8.1, Ar-H), 4.18 (t, 4H, J = 6.2, CH2-O-Ar), 3.67 (t, 2H, J = 6.3, CH2-O), 2.95 (s, 6H, CH3),2.67 (t, 2H, J = 7.8, Ar-CH2-), 2.27 (t, 2H, J = 6.1, -CH2-), 1.88 (t, 2H, J = 6.6, -CH2-), 1.57 (s, 1H,OH). 13C-NMR (100 MHz, CDCl3), (δ:ppm): 159.99, 157.15, 152.03, 133.93, 129.75, 129.32,114.50, 105.86, 102.18, 99.75, 64.34, 62.24, 40.65, 34.45, 31.17, 29.48. MS (ESI), (m/z) calcl.329.43; found: 330.31 [M + H]+. Elemental Analysis: (Found: C 73.12, H 8.20, N 4.40%, C20H27NO3(329.43) requires C 72.92, H 8.26, N 4.25%).

Reference： [1]Biyiklioglu, Zekeriya; Alp, Hakan [Journal of Coordination Chemistry, 2017, vol. 70, # 14, p. 2359 - 2370]

84
[ 10210-17-0 ]
[3-(3-chloropropoxy)phenyl]diethylamine [ No CAS ]
3-(4-{3-[3-(diethylamino)phenoxy]propoxy}phenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With 18-crown-6 ether; potassium carbonate In acetone for 48h; Reflux; Inert atmosphere;	2.1.1. 3-(4-{3-[3-(Dimethylamino)phenoxy]propoxy}phenyl)propan-1-ol (3) General procedure: 3-(4-Hydroxyphenyl)-1-propanol (1 g, 6.58 mmol), dried K2CO3 (0.9 g, 6.58 mmol), 18-crown-6(0.173 g, 0.658 mmol) and [3-(3-chloropropoxy)phenyl]dimethylamine1 (1.4 g, 6.58 mmol)in acetone (50 mL) were heated at reflux and stirred vigorously under nitrogen for 48 h. Thevolatile materials were removed under reduced pressure and the residue was treated with100 mL CHCl3 and 50 mL H2O. The separated water was extracted three times with 100 mLCHCl3. The combined organic phases were dried with MgSO4 and the crude product waspurified by aluminum oxide column chromatography with CHCl3 as solvent

Reference： [1]Biyiklioglu, Zekeriya; Alp, Hakan [Journal of Coordination Chemistry, 2017, vol. 70, # 14, p. 2359 - 2370]

85
[ 10210-17-0 ]
[ 402-23-3 ]
[ 134561-28-7 ]

Yield	Reaction Conditions	Operation in experiment
84.72%	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With potassium carbonate In acetone at 60℃; for 0.25h; Inert atmosphere; Stage #2: 1-bromomethyl-3-trifluoromethylbenzene With 18-crown-6 ether In acetone for 48h; Inert atmosphere; Reflux;	Synthesis of 3-(4-[3-(trifluoromethyl)benzyl]oxy}phenyl)propan-1-ol (3) 4-(3-Hydroxypropyl)phenol 1 (1 g, 6.57 mmol) was dissolved 50 ml of acetone under N2 atmosphere. Anhydrous K2CO3(1.03 g, 7.49 mmol) was added to reaction mixture then stirring at 60 °C for 15 min. 2 ml 1-(bromomethyl)-3-(trifluoromethyl)benzene 2 (1.79 g, 7.49 mmol) and 18-crown-6 (0.19 g, 0.73 mmol) was added to this solution. The reaction mixture was refluxed under nitrogen for 48 h. After the mixture was cooled, the solvent was removed under vacuum, and the resulting crude product was dissolved in 70 ml of chloroform (CHCl3). The mixture was washed with 35 ml of water. The organic phase was dried over magnesium sulphate (MgSO4), filtered and rotary evaporated. The obtained oily crude product was purified using column chromatography with basic aluminium oxide as the column material and a chloroform/methanol (10:2) solvent system. Yield: 1.72 g (84.72%). IR (KBr tablet), νmax/cm-1: 3371(Aliph-OH), 3031 (Ar-H), 2933-2868 (Aliph. C-H), 1611(C=C), 1328, 1119-1072 (C-O-C), 906 (C-H), 798, 698.1H-NMR. (CDCl3), (δ: ppm): 7.74 (s, 2H, Ar-H), 7.63-7.51(m, 2H, Ar-H), 7.27 (d, 2H, Ar-H), 6.95 (d, 2H, Ar-H), 5.09(s, 2H, -O-CH2-Ar), 3.71 (m, 2H, -O-CH2), 3.54 (s, 1H,O-H), 2.70 (t, 2H, -CH2), 1.93 (m, 2H, -CH2) (Fig. 1). 13CNMR. (CDCl3), (δ: ppm): 156.73 (C=C), 138.27 (C=C),134.56 (C=C), 132.38 (C=C), 131.07 (C=C), 130.63(C=C),129.47 (C=C), 129.06 (C=C), 124.73 (C=C), 124.09(C=C), 122.77 (C=C), 114.81 (C=C), 69.26 (F3-C-Ar),64.24 (O-CH2-Ar), 62.16 (O-CH2), 34.19 (CH2-Ar),31.13 (CH2-CH2). MS (ESI), (m/z): Calculated: 310.32 ;Found: 310.19 [M]+. Elemental Analysis, Anal, calc. forC17H17O2F3:C, 65.78; H, 5.48; Found: C, 65.90; H, 5.00%.

Reference： [1]Aktaş Kamiloğlu, Ayşe; Akyüz, Duygu; Koca, Atıf; Acar, İrfan [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2018, vol. 92, # 1-2, p. 223 - 235]

86
[ 366016-66-2 ]
[ 10210-17-0 ]
(E)-3-(4-((2-(4-(trifluoromethyl)styryl)oxazol-4-yl)methoxy)phenyl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.186 mg	Stage #1: 3-(4-hydroxyphenyl)propan-1-ol With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: 4-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)-phenyl]ethenyl]-1,3-oxazole In N,N-dimethyl-formamide at 20℃; for 2h;	6.1 To a solution of 4-(3-hydroxypropyl)phenol (116 mg, 0.765 mmol) in DMF (6953 μΙ) was added NaH (64.0 mg, 1.599 mmol). After 30 min, (E)-4-(chloromethyl)-2-(4-(trifluoromethyl)styryl)oxazole (200 mg, 0.695 mmol) was added to the chilled solution. After 2h at rt the mixture was poured into water and extracted with EA. The organic layer was washed with water, 1 N NaOH then brine, dried over Na2SC> , filtered and concentrated. The residue was adsorbed onto silica gel and purified by ISCO using a RediSep column (Hx_EA; 0-100%) to afford 0.186 mg of the title compound. LRMS + H+: 404.3.

Reference： [1]Current Patent Assignee: UNIVERSITY OF MONTREAL - WO2019/84662, 2019, A1 Location in patent: Page/Page column 125

87
[ 10210-17-0 ]
5-(chloromethyl)-1-(4-fluorophenyl)-3-methyl-1H-pyrazole-4-carbonitrile [ No CAS ]
1-(4-fluorophenyl)-5-[[4-(3-hydroxypropyl)phenoxy]methyl]-3-methyl-1H-pyrazole-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium carbonate at 80℃; for 4h;	87 Method A General procedure: A mixture of the chloride 4 (1.0 eq), the appropriate alcohol (1.0 eq), and K2CCh or Cs2C03 (2.0 eq) in acetonitrile or A, A- d i m c t h y 1 fo r m a m i d c was stirred for a time period between 2h and overnight at a temperature ranging between room temperature and the reflux temperature. After cooling to rt, H20 was added and the reaction mixture was extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over Na2S04, filtered and evaporated under vacuum. The desired product was obtained after purification of the crude material as reported in the specific examples.

Reference： [1]Current Patent Assignee: AXXAM S.P.A. - WO2019/175152, 2019, A1 Location in patent: Page/Page column 36-37; 72

88
[ 10210-17-0 ]
[ 109-64-8 ]
3-(4-bromopropoxyphenyl)propanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46.5%	With sodium hydrogencarbonate In ethanol at 50℃; for 5h;	16.b (b) 3-(4-bromopropoxyphenyl)propanol [0242] 30 g (0.197 mol) of the product (a) was dissolved in 300 mL of ethanol. 22.4 (0.26 mol) of sodium bicarbonate was added. 161.6 g (0.80 mol) of 1,3-dibromopropane was added at the same time. The reaction mixture was heated and stirred. The reaction was carried out at 50 °C for 5 hours. The solvent and excess 1,3-dibromopropane were removed under reduced pressure. The residue was dissolved in 250 mL of dichloromethane, washed with water three times (100 mL3), and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the solvent was removed under reduced pressure to obtain 25 g of the target compound with a yield of 46.5%. m/z 273.03, 275.04(M+H).

Reference： [1]Current Patent Assignee: BEIJING SHOWBY PHARMACEUTICAL - EP3556435, 2019, A1 Location in patent: Paragraph 0242

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CAS No. :	10210-17-0	MDL No. :	MFCD00002953
Formula :	C₉H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NJCVPQRHRKYSAZ-UHFFFAOYSA-N
M.W :	152.19	Pubchem ID :	82452
Synonyms :	Dihydro-p-coumaryl alcohol;3-(p-Hydroxyphenyl)propyl alcohol

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	44.21
TPSA :	40.46 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.34 cm/s

Log Po/w (iLOGP) :	1.59
Log Po/w (XLOGP3) :	1.25
Log Po/w (WLOGP) :	1.32
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	1.86
Consensus Log Po/w :	1.51

[ CAS No. 10210-17-0 ] {[proInfo.proName]}

Quality Control of [ 10210-17-0 ]

Related Doc. of [ 10210-17-0 ]

Product Details of [ 10210-17-0 ]

Calculated chemistry of [ 10210-17-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 10210-17-0 ]

Application In Synthesis of [ 10210-17-0 ]

[ 10210-17-0 ] Synthesis Path-Upstream 1~1

[ 10210-17-0 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.78
Solubility :	2.54 mg/ml ; 0.0167 mol/l
Class :	Very soluble
Log S (Ali) :	-1.7
Solubility :	3.05 mg/ml ; 0.02 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.44
Solubility :	0.548 mg/ml ; 0.0036 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling