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[ CAS No. 5597-50-2 ]

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Chemical Structure| 5597-50-2
Chemical Structure| 5597-50-2
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CAS No. :5597-50-2 MDL No. :MFCD00071577
Formula : C10H12O3 Boiling Point : 108°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :180.20 g/mol Pubchem ID :79706
Synonyms :

Safety of [ 5597-50-2 ]

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:

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[ 5597-50-2 ] Synthesis Path-Upstream   1~45

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  • [ 62803-47-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 27, p. 7751 - 7755[2] Angew. Chem., 2016, vol. 128, p. 7882 - 7886,5
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Reference: [1] Chemische Berichte, 1917, vol. 50, p. 618[2] Chem. Zentralbl., 1916, vol. 87, # II, p. 1025
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YieldReaction ConditionsOperation in experiment
99% With palladium on activated charcoal; hydrogen In ethanol at 20℃; for 21 h; Methyl 3-(4-hydroxyphenyl)propanoate (0413) (0414) To a solution of (E)-methyl 3-(4-hydroxyphenyl)acrylate (1.0 g, 5.6 mmol) in EtOH (20 mL), Pd/C (0.1 g) was added. The reaction mixture was vigorously stirred under hydrogen atmosphere (1 bar) at room temperature for 21 h. The suspension was filtered through a Celite pad and evaporated to dryness under vacuum to afford 1.0 g (5.6 mmol, 99percent yield) of an oil identified as methyl 3-(4-hydroxyphenyl)propanoate. (0415) 1H NMR (400 MHz, CDCl3) δ 7.07 (ddd, J=8.8, 2.8, 2.0 Hz, 2H), 6.76 (ddd, J=8.8, 2.8, 2.0 Hz, 2H), 4.72 (br s, 1H), 3.67 (s, 3H), 2.88 (t, J=7.8 Hz, 2H), 2.60 (t, J=7.8 Hz, 2H).
Reference: [1] Journal of Natural Products, 1999, vol. 62, # 1, p. 102 - 106
[2] Patent: EP2745876, 2014, A1, . Location in patent: Page/Page column
[3] Patent: US2015/344408, 2015, A1, . Location in patent: Paragraph 0413-0415
[4] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 26, p. 10635 - 10640
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7785 - 7788[6] Angew. Chem., 2014, vol. 53, # 30, p. 7919 - 7922,4
[7] Phytochemistry (Elsevier), 1992, vol. 31, # 4, p. 1179 - 1184
[8] Journal of the American Chemical Society, 2006, vol. 128, # 10, p. 3324 - 3334
[9] Synthetic Communications, 2011, vol. 41, # 11, p. 1603 - 1608
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YieldReaction ConditionsOperation in experiment
100% at 25℃; for 24 h; General procedure: To a suspension of 3(4-hydroxyphenyl)propanoic acid 1 (0.05 mmol) in TMCS (0.1 mmol), the appropriate alcohol (1.0 mL) was added and the reaction mixture was stirred at 25°C. After 24 h, the reaction was stopped and evaporated under reduced pressure to afford 1a–d in quantitative yield without the need of purification: 3-(4-Hydroxyphenyl)propionic acid methyl ester(1a) Oil; 1HNMR (400 MHz, CDCl3): δ H (ppm) = 2.66 (2H, m, CH2),3.05 (2H, m, CH2),3.65 (3H, m, OCH3), 6.73 (2H, m, Ph-H), 7.04(2H, m, Ph-H); 13C NMR (50 MHz, CDCl3): δ C (ppm) = 30.19 (CH2),35.23 (CH2), 50.99 (CH3),115.57 (2 CH), 129.54 (2 CH),131.59 (C), 155.71 (C), 172.74 (CO); MS (EI): m/z 252; Elemental analysis: calcd C, 66.65; H, 6.71; O, 26.64, found C, 66.64; H, 6.71;O, 26.63.
100% With acetyl chloride In methanol at 0℃; for 1.5 h; To a solution of3-(4-hydroxyphenyl)propanoic acid (2.50g, 15.04 mmol) in methanol(40 mL) were added dropwise 5.35 mL acetyl chloride (5.0eq,75.20 mmol) at 0 °C. The reaction mixture was stirred over 1.5 h at0 °C. After completion of the reaction, the mixture was concentratedin vacuo and ethyl acetate was added. The organic layer waswashed with NaHCO3 (3 x 50 mL) and concentrated in vacuo to givemethyl 3-(4-hydroxyphenyl)propanoate 38 (2.70 g, 100percent) as acolorless oil. UPLC-MS: 1.62 min, 100percent. 1H NMR (300 MHz, CD3OD) δ (ppm) 7.08-6.94 (m, 2H), 6.80-6.64 (m, 2H), 3.69-3.49 (m, 3H),2.87-2.70 (m, 2H), 2.60-2.45 (m, 2H). 13C NMR (75 MHz, CD3OD) δ (ppm) 174.4, 155.8, 131.8, 129.3, 115.3, 51.1, 36.1, 30.2. MS (ES) m/z181.7 (M + H)+. HRMS calculated for C10H12O3: 203.0679; found:203.0679 (M + Na)+.
99% With hydrogenchloride In 1,4-dioxane at 20℃; for 3 h; [355] Preparation Example 4: 3-(4-hydroxy-phenyl)-propionic acid methyl ester[356] After 3-(4-hydroxy-phenyl)propionic acid (3 g, 18 mmol) was added with MeOH(6 mL), 4M HCl/dioxane solution (18 mL, 72 mmol) was added thereto, and themixture was stirred at room temperature for 3 hours. The reactant wasconcentrated, added with EtOAc, and then washed with NaCl aqueous solution. Theorganic layer was separated, dried with MgSO4, and filtered toobtain the title compound (3.26 g, 99percent). [357] 1H-NMR (CDCl3) δ 7.06(2H, m), 6.75(2H, m),4.79(1H, brs, OH), 3.66(3H, s), 2.88(2H, t), 2.59(2H, t)
98% at 70℃; for 3 h; 4.61 g p-hydroxyphenpropionic acid, 50 ml methanol and 0.5 ml concentrated H2SO4 were refluxed at 70°C for 3 hours and cooled. Excessive acid was neutralized with saturated NaHCO3 solution. The neutralized solution was extracted with ethyl acetate for three times. The extract was dried, filtrated, evaporated and purified by column chromatograph (petroleum ether: ethyl acetate=2:1) to obtain 4.9 g white solid, yield 98percent. 1H-NMR (400MHz, DMSO-d6, δ ppm) δ 2.5(2H, m), 2.7(2H, t), 3.567(3H, s), 6.6(2H, d, J=6.4Hz), 7.0(2H, d, J=8.4Hz), 9.0(1H, s).
98% at 70℃; for 3 h; Intermediate 10: Methyl p-hydroxyphenpropionate
4.61 g p-hydroxyphenpropionic acid, 50 ml methanol and 0.5 ml concentrated H2SO4 were refluxed at 70° C. for 3 hours and cooled.
Excessive acid was neutralized with saturated NaHCO3 solution.
The neutralized solution was extracted with ethyl acetate for three times.
The extract was dried, filtrated, evaporated and purified by column chromatograph (petroleum ether:ethyl acetate=2:1) to obtain 4.9 g white solid, yield 98percent. 1H-NMR (400 MHz, DMSO-d6, δ ppm) δ 2.5 (2H, m), 2.7 (2H, t), 3.567 (3H, s), 6.6 (2H, d, J=6.4 Hz), 7.0 (2H, d, J=8.4 Hz), 9.0 (1H, s).
98% for 16 h; Reflux General procedure: According to a literature protocol.[1] Propanoic acid derivative (10 g) was dissolved inmethanol (80 ml) and H2SO4 (700μl, 6 mmol) added. The resulting solution was refluxed for16 h and then allowed to cool to room temperature. The reaction mixture was reduced todryness and re-dissolved in ethyl acetate (20 ml). The organic phase was washed withsaturated aqueous sodium hydrogen carbonate (10 ml), brine (10 ml) and dried over MgSO4.Removal of the solvent gave the desired methyl ester. (Note: column chromatography is oftennot required for the methyl ester starting materials). Methyl 3-(4-hydroxyphenyl)propanoate (1a) Synthesized according to general procedure A (98percent); 1H NMR (500 MHz, d4-MeOH): δ 6.98(d, J = 8.4 Hz, 2H), 6.66 (d, J = 8.4 Hz, 2H), 3.60 (s, 3H), 2.78 (t, J = 7.6 Hz, 2H), 2.53 (t, J= 7.6 Hz, 2H); 13C NMR (125 MHz, d4-MeOH): 172.8, 155.6, 130.6, 129.1, 115.1, 51.2, 35.4,29.5; HRMS (EI) calculated for C10H12O3 [M]+: 180.078643; found: 180.078803.
98.2% for 10 h; Reflux 20 g of p-hydroxyphenylpropionic acid was added to 300 ml of anhydrous methanol and2 ml of concentrated sulfuric acid, heated to reflux for 10 h, the solvent was evaporated under reduced pressure, then dissolved with ethyl acetate and washed sequentially with sodium hydrogen carbonate and water.Polyester, organic layer dried over anhydrous magnesium sulfate,The solvent was evaporated to give 21.2 g (yield: 98.2percent).
92% at 20℃; for 16 h; 15 g (0.09 mol, 1 eq) of 3-(4-hydroxyphenyl)propanoic acid are dissolved in 50 ml of methanol and 4 drops of sulfuric acid are added. The reaction mixture is stirred for 16 hours at room temperature. The reaction is stopped by addition of 50 mL of saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 14.9 g of methyl 3-(4-hydroxyphenyl)propanoate are obtained. Yield = 92 percent
84% at 20℃; for 8 h; To a solution of 3-(4-hydroxyphenyl)propanoic acid (3 g, 18.1 mmol) in 50 mL MeOH was added ΒΡ3·Ε20 (0.3 mL). The mixture was stirred at rt for 8 h. The mixture was concentrated, and the residue was purified by flash chromatography (FC) (ethyl acetate (EtOAc) /hexane = 2/8) to give 2.72 g white solid A (yield: 84percent): 1HNMR(400 MHz, CDC13) δ: 7.07(d, 2H, J= 8.4 Hz), 6.76(d, 2H, J= 8.4 Hz), 4.72(s, 1H), 3.68(s, 3H), 2.89(t, 2H, J= 7.6 Hz), 2.60(t, 2H, J= 7.6 Hz). HRMS (ESI) calculated for C10H13O3 (M+H+), 181.0865; found, 181.0889
68% for 12 h; Heating / reflux 0. 8g 4-hydroxy cinnamic acid in 40 ml methanol and 10 drops HCl were refluxed for 12 hours. Workup as above gave 0.6g oil, 68percent yield. NMR CDC13 7.02, 6.75 (4H, Abq, J=8.6 Hz), 3.66 (3H, s), 2.86 (2H, t, J=7.4 Hz), 2.60 (2H, t, J=7. 4 Hz).
68% for 12 h; Heating / reflux AV 32 [ CNHISNOG] Mol. Wt.: 209.24 A. 0.8 gr 4-hydroxy cinnamic acid in 40 [ML METHANOL] and 10 drops HCI were [REFLUXED] for 12 hours. Workup as above gave 0.6 gr oil, 68percent yield. NMR CDCl3 7.02, 6.75 (4H, Abq, J=8.6 Hz), 3.66 (3H, s), 2.86 (2H, t, J=7.4 [HZ),] 2.60 (2H, t, J=7. 4 Hz). B. 0.6 gr, 3.3 mM, ester from step A and 0.26 gr, 4.2 mM, ethanol amine were heated at 100 for 3 hours in an open vessel. Chromatography gave 0.3 gr recovered ester followed by amide. The viscous oil was triturated with acetone-methylene chloride and filtered to give 160 mg white solid, 23percent yield, mp-102. NMR acetone d6 8.10 (1H, s, OH), 7. [03,] 6.74 (4H, Abq, J=8. [8 HZ),] 3.90 (1H, t, J=5.2 Hz, NH), 3.54 (2H, q, J=7.1 Hz), 3.28 (2H, t, J=7.1 [HZ),] 2.80 (2H, t, J=8.2 Hz), 2.41 (2H, t, J=8.2 Hz).
68% for 12 h; Heating / reflux 0. 8g 4-hydroxy cinnamic acid in 40 ml methanol and 10 drops HCl were refluxed for 12 hours. Workup as above gave 0.6g oil, 68percent yield. NMR CDC13 7.02, 6.75 (4H, Abq, J=8.6 Hz), 3.66 (3H, s), 2.86 (2H, t, J=7.4 Hz), 2.60 (2H, t, J=7. 4 Hz).
62% for 24 h; Reflux General procedure: After dissolving the carboxylic acid in the alcohol, three drops of H2SO4 95percent were added to the solution and the mixture was refluxed for 24 h. The solvent was evaporated under reduced pressure and water was added to the crude mixture. The pH of the aqueous layer was adjusted to 7 adding drops of a saturated solution of NaHCO3 and brine was added in the mixture. The aqueous layer was extracted three times with ethyl acetate; the organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure yielding the final compound. Further purification step was made when it was necessary.
21.2 g at 0℃; Inert atmosphere 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 15percent 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).
365.8 g for 7 h; Reflux 2L three-mouth bottle, is provided with a stirring, thermometer and a condenser. Adding 340.0g the hydroxy phenylpropanoic acid, 3.4g concentrated sulfuric acid and 1500 ml methanol, heating reflux for 7 hours. Cooling to room temperature, using NaHCO 3 solution to neutral, rotary evaporimeter desolventizing, by adding 600 ml of water and 600 ml toluene, liquid separation, the organic phase washed to neutral, and to obtain the product solvent 365.8g, GC purity: 98.4percent.

Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 21, p. 3351 - 3354
[2] Journal of Organic Chemistry, 2009, vol. 74, # 11, p. 4236 - 4241
[3] Organic Letters, 2013, vol. 15, # 23, p. 6058 - 6061
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5345 - 5351
[5] Organic Letters, 2016, vol. 18, # 11, p. 2600 - 2603
[6] European Journal of Medicinal Chemistry, 2017, vol. 129, p. 110 - 123
[7] Synlett, 2018, vol. 29, # 9, p. 1239 - 1243
[8] Tetrahedron Asymmetry, 1993, vol. 4, # 2, p. 261 - 272
[9] Patent: WO2014/69963, 2014, A1, . Location in patent: Paragraph 355-357
[10] Patent: EP2952517, 2015, A1, . Location in patent: Paragraph 0217
[11] Patent: EP2184277, 2010, A1, . Location in patent: Page/Page column 13
[12] Patent: US2011/9427, 2011, A1, . Location in patent: Page/Page column 8
[13] Tetrahedron Letters, 2013, vol. 54, # 25, p. 3294 - 3297
[14] Patent: CN108640834, 2018, A, . Location in patent: Paragraph 0020; 0028; 0029; 0034
[15] Organic Letters, 2003, vol. 5, # 13, p. 2215 - 2217
[16] Tetrahedron, 2005, vol. 61, # 30, p. 7144 - 7152
[17] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2034 - 2039
[18] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 4, p. 428 - 432
[19] Organic and Biomolecular Chemistry, 2003, vol. 1, # 9, p. 1486 - 1497
[20] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 1-2, p. 89 - 115
[21] Tetrahedron, 1990, vol. 46, # 20, p. 7105 - 7118
[22] Analytical Chemistry, 2002, vol. 74, # 2, p. 468 - 478
[23] Patent: WO2006/18326, 2006, A1, . Location in patent: Page/Page column 22
[24] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 17, p. 9476 - 9482
[25] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 11, p. 1225 - 1234
[26] Organic and Biomolecular Chemistry, 2015, vol. 13, # 22, p. 6225 - 6241
[27] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 332 - 344
[28] Patent: WO2017/116994, 2017, A1, . Location in patent: Paragraph 0072
[29] Bioconjugate Chemistry, 2016, vol. 27, # 5, p. 1314 - 1323
[30] Synthetic Communications, 2012, vol. 42, # 5, p. 722 - 726
[31] Patent: WO2005/92305, 2005, A2, . Location in patent: Page/Page column 25
[32] Patent: WO2004/31129, 2004, A2, . Location in patent: Example 1
[33] Patent: WO2005/92305, 2005, A2, . Location in patent: Page/Page column 25
[34] Bulletin of the Polish Academy of Sciences, Chemistry, 1986, vol. 34, # 3-4, p. 115 - 122
[35] European Journal of Medicinal Chemistry, 2015, vol. 90, p. 351 - 359
[36] Chemische Berichte, 1917, vol. 50, p. 618[37] Chem. Zentralbl., 1916, vol. 87, # II, p. 1025
[38] Tetrahedron, 1966, vol. 22, p. 861 - 866
[39] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1173 - 1187
[40] Journal of Medicinal Chemistry, 1982, vol. 25, # 12, p. 1408 - 1412
[41] Gazzetta Chimica Italiana, 1996, vol. 126, # 2, p. 121 - 125
[42] Tetrahedron, 1997, vol. 53, # 12, p. 4387 - 4410
[43] Synthetic Communications, 1998, vol. 28, # 4, p. 747 - 751
[44] Journal of Agricultural and Food Chemistry, 1998, vol. 46, # 4, p. 1670 - 1676
[45] Patent: WO2005/16862, 2005, A1, . Location in patent: Page/Page column 411
[46] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 316
[47] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 152
[48] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1939 - 1944
[49] Patent: US2004/44258, 2004, A1, . Location in patent: Page 57
[50] Patent: WO2003/95441, 2003, A1, . Location in patent: Page/Page column 15
[51] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 7, p. 345 - 349
[52] Journal of Materials Chemistry A, 2013, vol. 1, # 6, p. 2256 - 2266
[53] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7699 - 7708
[54] Patent: US2013/323271, 2013, A1, . Location in patent: Paragraph 0387; 0388
[55] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6874 - 6878
[56] Patent: CN103539640, 2016, B, . Location in patent: Paragraph 0070; 0082; 0083
[57] Patent: CN107721836, 2018, A, . Location in patent: Paragraph 0043; 0044-0046
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YieldReaction ConditionsOperation in experiment
95.9%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: at 0 - 20℃; for 3 h;
Intermediate 2: Methyl 3-(4-hydroxyphenyl) propanoateTo a 1000 mL RB flask fitted with magnetic stirrer was charged 250 mL of DMF, 3-(4- Hydroxy-phenyl)-propanoic acid (25.0 g, 150.43 mmol) and K2C03 (41.58 g, 300.87 mmol). The resulting mixture was stirred at RT for 30 minutes. Methyl Iodide (25.627 g, 180.51 mmol) was added to the resulting mixture which was precooled to 0 3/4. The resulting mixture was stirred at RT for 3 h. After completion of the reaction (reaction monitored by TLC), the solvent was removed under reduced pressure and the crude mass was dissolved in ethyl acetate (250 mL). The organic layer was washed with water (250 mL), saturated sodium bicarbonate solution (250 mL X 2), and saturated brine solution (250 mL). The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure. The product was obtained as yellow color oil (26 g, Yield: 95.9 percent): MS (ESI, 120 eV) : m/z = 178.9 (M- H)+; 1H NMR (300MHz, CDCI3): δ 6.97-7.00(d, 2H), 6.66-6.69(d, 2H), 4.94(s, 1 H), 3.59(s, 3H), 2.78-2.83(t, 2H), 2.50-2.55(t, 2H).
Reference: [1] Synthetic Communications, 2005, vol. 35, # 1, p. 145 - 152
[2] Patent: WO2012/11125, 2012, A1, . Location in patent: Page/Page column 59; 60
[3] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 6, p. 1462 - 1469
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  • [ 7400-08-0 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 10, p. 3324 - 3334
[2] Analytical Chemistry, 2002, vol. 74, # 2, p. 468 - 478
[3] Journal of Natural Products, 1999, vol. 62, # 1, p. 102 - 106
[4] Bulletin of the Polish Academy of Sciences, Chemistry, 1986, vol. 34, # 3-4, p. 115 - 122
[5] Phytochemistry (Elsevier), 1992, vol. 31, # 4, p. 1179 - 1184
[6] Patent: US5571506, 1996, A,
[7] Patent: EP2745876, 2014, A1,
[8] Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7785 - 7788[9] Angew. Chem., 2014, vol. 53, # 30, p. 7919 - 7922,4
[10] Patent: US2015/344408, 2015, A1,
  • 7
  • [ 3943-97-3 ]
  • [ 5597-50-2 ]
Reference: [1] Canadian Journal of Chemistry, 2012, vol. 90, # 9, p. 758 - 761
[2] Pharmazie, 2010, vol. 65, # 12, p. 913 - 918
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4608 - 4617
  • 8
  • [ 475272-11-8 ]
  • [ 5597-50-2 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 33, p. 6317 - 6320
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YieldReaction ConditionsOperation in experiment
80% With sulfuric acid In methanol; silica gel; toluene (a)
Methyl 3-(4-Hydroxyphenyl)propionate
A solution of 17 gm (0.1 mole) of 3-(4-hydroxyphenyl)propionic acid in 500 ml methanol and 2 ml concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3 A molecular sieves.
The solution was heated to reflux for 72 hours and the sieves were exchanged at 24 hours intervals.
The reaction medium was then evaporated to an oil which was dissolved in 100 ml toluene and extracted with 3*100 ml water.
The toluene phase was dried over magnesium sulfate, treated with activated charcoal and evaporated to provide 15 gm (80percent) of a clear oil.
The NMR spectrum was consistent with the assigned structure and this material was utilized directly in the next reaction step.
80% With sulfuric acid In methanol; silica gel; toluene Methyl 3-(4-Hydroxyphenyl)propionate
A solution of 17 gm (0.1 mole) of 3-(4-hydroxyphenyl)propionic acid in 500 mL methanol and 2 mL concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3 A molecular sieves.
The solution was refluxed for 72 hours and the sieves were exchanged at 24 hour intervals.
The reaction medium was then evaporated to an oil which was dissolved in 100 mL toluene and extracted with 3*100 mL water.
The toluene phase was dried over magnesium sulfate, treated with activated charcoal and evaporated to provide 15 gm (80percent) of a clear oil.
The NMR spectrum was consistent with the assigned structure and this material was utilized directly in the next reaction step.
Reference: [1] Patent: US4623652, 1986, A,
[2] Patent: US4387103, 1983, A,
  • 10
  • [ 23795-02-0 ]
  • [ 5597-50-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 27, p. 7751 - 7755[2] Angew. Chem., 2016, vol. 128, p. 7882 - 7886,5
  • 11
  • [ 501-97-3 ]
  • [ 616-38-6 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11606 - 11611
  • 12
  • [ 501-97-3 ]
  • [ 77-78-1 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 10, p. 3606 - 3609
  • 13
  • [ 61240-27-5 ]
  • [ 5597-50-2 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6145 - 6148
  • 14
  • [ 6386-38-5 ]
  • [ 128-39-2 ]
  • [ 5597-50-2 ]
  • [ 36837-50-0 ]
Reference: [1] Patent: CN107011149, 2017, A, . Location in patent: Paragraph 0064-0067
  • 15
  • [ 67-56-1 ]
  • [ 7400-08-0 ]
  • [ 5597-50-2 ]
Reference: [1] Synlett, 2003, # 1, p. 87 - 90
  • 16
  • [ 540-38-5 ]
  • [ 292638-85-8 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1529 - 1541
  • 17
  • [ 195454-08-1 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
  • 18
  • [ 501-97-3 ]
  • [ 5597-50-2 ]
Reference: [1] Patent: US4450173, 1984, A,
  • 19
  • [ 67-56-1 ]
  • [ 1588490-32-7 ]
  • [ 5597-50-2 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 8, p. 2248 - 2251
  • 20
  • [ 501-97-3 ]
  • [ 149-73-5 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 22, p. 4894 - 4903
  • 21
  • [ 195454-08-1 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
  • 22
  • [ 7400-08-0 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4608 - 4617
  • 23
  • [ 195454-06-9 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
[2] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
  • 24
  • [ 195454-05-8 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
[2] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
  • 25
  • [ 195454-07-0 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
[2] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6726 - 6729
  • 26
  • [ 103-25-3 ]
  • [ 5597-50-2 ]
  • [ 20349-89-7 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 16, p. 8084 - 8095
  • 27
  • [ 77092-56-9 ]
  • [ 5597-50-2 ]
Reference: [1] Tetrahedron, 1980, vol. 36, # 10, p. 1301 - 1306
  • 28
  • [ 106-41-2 ]
  • [ 5597-50-2 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 8, p. 2248 - 2251
  • 29
  • [ 67-56-1 ]
  • [ 2628-16-2 ]
  • [ 201230-82-2 ]
  • [ 54965-55-8 ]
  • [ 5597-50-2 ]
  • [ 65784-33-0 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 63, p. 12574 - 12577
[2] Chemical Communications, 2015, vol. 51, # 63, p. 12574 - 12577
  • 30
  • [ 1929-29-9 ]
  • [ 5597-50-2 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 1998, vol. 46, # 4, p. 1670 - 1676
[2] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1173 - 1187
  • 31
  • [ 123-08-0 ]
  • [ 5597-50-2 ]
Reference: [1] Synthetic Communications, 2011, vol. 41, # 11, p. 1603 - 1608
  • 32
  • [ 2979-06-8 ]
  • [ 5597-50-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 27, p. 7751 - 7755[2] Angew. Chem., 2016, vol. 128, p. 7882 - 7886,5
  • 33
  • [ 106-44-5 ]
  • [ 5597-50-2 ]
Reference: [1] Patent: CN108640834, 2018, A,
  • 34
  • [ 140-39-6 ]
  • [ 5597-50-2 ]
Reference: [1] Patent: CN108640834, 2018, A,
  • 35
  • [ 52727-95-4 ]
  • [ 5597-50-2 ]
Reference: [1] Patent: CN108640834, 2018, A,
  • 36
  • [ 830-09-1 ]
  • [ 5597-50-2 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1173 - 1187
  • 37
  • [ 6386-38-5 ]
  • [ 5597-50-2 ]
  • [ 36837-50-0 ]
  • [ 115-11-7 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 4, p. 681 - 684[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 4, p. 752 - 756
  • 38
  • [ 186581-53-3 ]
  • [ 501-97-3 ]
  • [ 5597-50-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1963, vol. 663, p. 74 - 82
  • 39
  • [ 5597-50-2 ]
  • [ 100-39-0 ]
  • [ 24807-40-7 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In acetonitrile for 1 h; Reflux Methyl 3-[4-(benzyloxy)phenyl]propanoate; BnBr (4.39 g, 25.64 mmol) was added to a suspension of K2CO3 (3.55 g, 25.64 mmol) and methyl 3-(4-hydroxyphenyl)propanoate (1.54 g, 8.55 mmol) in CH3CN (40 ml_). The reaction mixture was warmed up to reflux, and allowed to react for 1 h. It was poured into H2O (120 ml_), taken up to pH = 2 with HCI (10percent aqueous solution) and extracted with EtOAc (2x100 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (0-->5percent EtOAc/hexanes) to give 2.01 g of methyl 3-[4- (benzyloxy)phenyl]propanoate (white solid, yield: 88percent).1 H NMR (CDCI3, 250 MHz) δ ppm: 7.51 -7.29 (m, 5H), 7.14 (d, J = 8.8 Hz, 2H), 6.92 (d, J = 8.8 Hz, 2H), 5.05 (s, 2H), 3.69 (s, 3H), 2.92 (t, J = 7.6 Hz, 2H), 2.62 (t, J = 7.6 Hz, 2H).
Reference: [1] Patent: US2002/65246, 2002, A1,
[2] Patent: US6414179, 2002, B1,
[3] Patent: WO2010/70076, 2010, A1, . Location in patent: Page/Page column 104
[4] Patent: EP2952517, 2015, A1, . Location in patent: Paragraph 0217
[5] Bulletin of the Polish Academy of Sciences, Chemistry, 1986, vol. 34, # 3-4, p. 115 - 122
[6] Journal of Medicinal Chemistry, 2001, vol. 44, # 21, p. 3351 - 3354
[7] Tetrahedron, 1973, vol. 29, p. 1405 - 1411
[8] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 316-317
[9] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 153
[10] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1939 - 1944
[11] Patent: WO2003/95441, 2003, A1, . Location in patent: Page/Page column 15-16
[12] Patent: EP1849465, 2007, A1, . Location in patent: Page/Page column 81
[13] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 7, p. 345 - 349
[14] RSC Advances, 2016, vol. 6, # 46, p. 40238 - 40249
[15] Patent: WO2008/130514, 2008, A1, . Location in patent: Page/Page column 104
  • 40
  • [ 5597-50-2 ]
  • [ 100-51-6 ]
  • [ 24807-40-7 ]
YieldReaction ConditionsOperation in experiment
59% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 2 h; Reference Example 1
Methyl 4-(phenylmethoxy)benzenepropanoate
To a solution of ice-cooled methyl 4-hydroxybenzenepropanoate (0.70 g, 3.9 mmol), benzyl alcohol (0.48 mL, 4.7 mmol) and triphenylphosphine (1.2 g, 4.7 mmol) in tetrahydrofuran (5 mL) was added dropwise diethyl azodicarboxylate (0.73 mL, 4.7 mmol), and the mixture was stirred for 2 hours with ice cooling.
To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate.
The extract was washed with water, and then concentrated under reduced pressure.
The residue was purified with silica gel column chromatography (hexane/ethyl acetate = 17: 3) to give the title compound (0.62 g, yield 59percent) as powders.
1H NMR (CDC13) δ 2.59 (2H, t, J=7.5 Hz), 2.89 (2H, t, J=7.5 Hz), 3.66 (3H, s), 5.04 (2H, s), 6.90 (2H, d, J=8.6 Hz), 7.11 (2H, d, J=8.6 Hz), 7.29-7.44 (5H, m).
59% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 2 h; Reference Example 1
methyl 4-(phenylmethoxy)benzenepropanoate
To an ice-cooled solution of methyl 4-hydroxybenzenepropanoate (0.70 g, 3.9 mmol), benzyl alcohol (0.48 mL, 4.7 mmol) and triphenylphosphine (1.2 g, 4.7 mmol) in tetrahydrofuran (5 mL) was added dropwise diethyl azodicarboxylate (0.73 mL, 4.7 mmol), and the mixture was stirred under ice-cooling for 2 hr.
Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.
The extract was washed with water and concentrated under reduced pressure.
The residue was purified by silica gel column chromatography (hexane/ethyl acetate=17:3) to give the title compound (0.62 g, yield 59percent) as a powder.
1H NMR (CDCl3) δ 2.59 (2H, t, J=7.5 Hz), 2.89 (2H, t, J=7.5 Hz), 3.66 (3H, s), 5.04 (2H, s), 6.90 (2H, d, J=8.6 Hz), 7.11 (2H, d, J=8.6 Hz), 7.29-7.44 (5H, m).
Reference: [1] Patent: EP1688138, 2006, A1, . Location in patent: Page/Page column 76
[2] Patent: EP1559422, 2005, A1, . Location in patent: Page/Page column 70
  • 41
  • [ 5597-50-2 ]
  • [ 100-44-7 ]
  • [ 24807-40-7 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 30, p. 7144 - 7152
[2] Tetrahedron, 1990, vol. 46, # 20, p. 7105 - 7118
[3] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2914,2916; engl. Ausg. S. 2875
[4] Journal of Medicinal Chemistry, 1977, vol. 20, # 11, p. 1388 - 1393
  • 42
  • [ 5597-50-2 ]
  • [ 81161-17-3 ]
Reference: [1] Synthetic Communications, 2012, vol. 42, # 5, p. 722 - 726
  • 43
  • [ 6386-38-5 ]
  • [ 128-39-2 ]
  • [ 5597-50-2 ]
  • [ 36837-50-0 ]
Reference: [1] Patent: CN107011149, 2017, A, . Location in patent: Paragraph 0064-0067
  • 44
  • [ 6386-38-5 ]
  • [ 5597-50-2 ]
  • [ 36837-50-0 ]
  • [ 115-11-7 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 4, p. 681 - 684[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 4, p. 752 - 756
  • 45
  • [ 5597-50-2 ]
  • [ 1374516-07-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4511 - 4515
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