3381-87-1|(2-(Benzyloxy)phenyl)methanol| Ambeed

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Quality Control of [ 3381-87-1 ] Purity: 98% SDS Specification

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Product Details of [ 3381-87-1 ]

CAS No. :	3381-87-1
Formula :	C₁₄H₁₄O₂
M.W :	214.26
SMILES Code :	OCC1=CC=CC=C1OCC2=CC=CC=C2
MDL No. :	MFCD01664428
InChI Key :	XRZMRABYCSOXIZ-UHFFFAOYSA-N
Pubchem ID :	18811

Safety of [ 3381-87-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H318
Precautionary Statements:	P280-P305+P351+P338
Class:	8
UN#:	1759
Packing Group:	Ⅲ

Application In Synthesis of [ 3381-87-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 3381-87-1 ]

[ 3381-87-1 ] Synthesis Path-Downstream 1~35

1
[ 89-84-9 ]
[ 3381-87-1 ]
[ 103633-37-0 ]
[ 103633-36-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1015 - 1022.

2
[ 3602-54-8 ]
[ 3381-87-1 ]
[ 103633-31-4 ]
[ 103633-32-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1015 - 1022.

3
[ 3381-87-1 ]
[ 103633-30-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With carbon tetrabromide; triphenylphosphine; In diethyl ether; dichloromethane; at -20 - 0℃; for 1h;	To a solution of <strong>[3381-87-1]2-benzyloxybenzyl alcohol</strong> (2.0 g, 9.3 mmol, 1.0 equiv) in CH2Cl2 (60 mL) at 0 C. was added PPh3 (3.67 g, 14.0 mmol, 1.5 equiv) and CBr4 (4.64 g, 14.0 mmol, 1.5 equiv). After 30 minutes the reaction was concentrated in-vacuo, then the residue was taken up in Et2O (50 mL) and placed at -20 C. for 30 minutes. The solution was filtered to remove solid Ph3PO and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (hexanes/EtOAc) afforded the title compound (2.28 g, 88%). Rf=0.75 (9:1 Hexane/EtOAc); 1H NMR (600 MHz, CDCl3) δ 4.62 (s, 2H), 5.16 (s, 2H), 6.80-7.10 (m, 2H), 7.20-7.55 (m, 7H); 13C NMR (150 MHz, CDCl3) δ 29.4, 70.3, 112.5, 121.2, 126.8, 127.4, 128.1, 128.8, 130.4, 131.2, 137.1, 156.8.
	With phosphorus tribromide; In diethyl ether;	C) To a solution of <strong>[3381-87-1]2-benzyloxybenzyl alcohol</strong> (4.83 g) in diethyl ether (40 ml) was added dropwise, at 0 C., a solution of phosphorus tribromide (6.27 g) in diethyl ether (10 ml). The mixture was warmed to ambient temperature, diluted with diethyl ether (100 ml) and filtered through a pad of silica gel washing with 1 litre of diethyl ether. The combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxybenzyl bromide (5.88 g) as an oil.

References: [1]Phytochemistry,1998,vol. 48,p. 893 - 896.
[2]Synthesis,2009,p. 4190 - 4202.
[3]Journal of Pharmacy and Pharmacology,2002,vol. 54,p. 349 - 364.
[4]Chemistry - A European Journal,2016,vol. 22,p. 7959 - 7963.
[5]Journal of Medicinal Chemistry,2006,vol. 49,p. 31 - 34.
[6]Patent: US2008/293666,2008,A1 .Location in patent: Page/Page column 36.
[7]ARKIVOC,2010,vol. 2010,p. 27 - 40.
[8]Chemical Communications,2016,vol. 52,p. 8467 - 8470.
[9]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1015 - 1022.
[10]Patent: US5811459,1998,A .
[11]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6816 - 6821.

4
[ 3381-87-1 ]
[ 23915-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In chloroform; at 20℃; for 1.5h;Inert atmosphere;	Preparation Example 28 Under an argon atmosphere, to a solution of [2-(benzyloxy)phenyl]methanol (20.2 g) in chloroform (160 ml) was slowly added a solution of thionyl chloride (13.8 ml) in chloroform (40 ml) at room temperature. After stirring at room temperature for 90 minutes, volatile substances were evaporated under reduced pressure to obtain 1-(benzyloxy)-2-(chloromethyl)benzene. Then, under an argon atmosphere, to a solution of di-tert-butyl iminodicarboxylate (41.0 g) in DMF (500 ml) was added potassium tert-butoxide (21.2 g) at room temperature. After stirring at the same temperature for 70 minutes, a solution of 1-(benzyloxy)-2-(chloromethyl)benzene in DMF (60 ml) was added thereto. After stirring at the same temperature for 15 hours, water was added thereto, followed by stirring for additional 90 minutes. The precipitate was collected by filtration, washed with water, and then dried under reduced pressure. The obtained crude product was purified by silica gel column chromatography (chloroform) to obtain 34.5 g of di-tert-butyl [2-(benzyloxy)benzyl]imidodicarbonate.

References: [1]Synthesis,2008,p. 3919 - 3924.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2022 - 2031.
[3]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 1267 - 1276.
[4]Journal of Pharmacy and Pharmacology,2002,vol. 54,p. 349 - 364.
[5]Liebigs Annalen,1996,p. 683 - 691.
[6]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208.
[7]Patent: EP2325175,2011,A1 .Location in patent: Page/Page column 30.
[8]Bulletin of the Korean Chemical Society,2016,vol. 37,p. 1509 - 1514.

5
[ 5896-17-3 ]
[ 3381-87-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 0.666667h;	To a solution of 2-benzyloxybenzaldehyde (1.00 g, 4.71 mmol, 1.0 equiv) in MeOH (25 mL) at 0 C. was added NaBH4 (0.40 g, 9.43 mmol, 2.0 equiv) portionwise over 10 minutes. After gas evolution ceased, the reaction mixture was warmed to room temperature and stirred for 30 minutes. The reaction was concentrated and the residue partitioned between H2O (50 mL) and EtOAc (50 mL). The organic phase was separated and the aqueous phase extracted with EtOAc (2×75 mL). The combined organic extracts were dried (Na2SO4) then concentrated to afford the title compound (0.98 g, 98%), which required no further purification. 1H NMR (600 MHz, CDCl3) δ 2.22 (br s, 1H), 4.73 (s, 2H), 5.12 (s, 2H), 6.92-7.00 (m, 2H), 7.24-7.29 (m, 1H), 7.29-7.37 (m, 2H), 7.37-7.44 (m, 4H). 13C NMR (150 MHz, CDCl3) δ62.4, 70.3, 111.9, 121.3, 127.6, 128.4, 129.0, 129.1, 129.2, 129.8, 137.0, 156.9.
90%	With sodium tetrahydroborate; In methanol; at 0℃; for 0.5h;	General procedure: NaBH4 (50 mg, 1.3 mmol) was added to a solution of commercial 2-phenoxybenzaldehyde (260 mg, 1.31 mmol) in MeOH (5 mL) at 0 C. After stirring for 30 min at 0 C, the reaction mixture was diluted with water, extracted with EtOAc, dried over MgSO4 and evaporated. The resulting residue was purified by column chromatography on silica gel (n-hexane/EtOAc = 5/1) to provide the title compound (228 mg, 1.14 mmol) in 87% yield as a colorless solid.
	With hydrogenchloride; sodium borohydrid; In ethanol; ethyl acetate;	(B) A mixture of 2-benzyloxybenzaldehyde (5 g, Apin) and sodium borohydride (1.4 g) in ethanol (50 ml) was stirred under argon for 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate and added dropwise to 0.1M hydrochloric acid solution (200 ml) at 0 C. The organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxybenzyl alcohol (4.91 g) as an oil.

	With hydrogenchloride; sodium tetrahydroborate; In ethanol;	Step L Preparation of 2-(benzyloxy)benzyl alcohol To a stirring solution of 2-(benzyloxy)benzaldehyde (10 g, 47 mmol) in 100 mL of Ethanol, NaBH4 was added as a solid in small portions. The reaction temperature was controlled with a room temperature water bath. After stirring for 30 minutes, the reaction was quenched by slow addition of 3N HCl. This solution was extracted with EtOAc and the organic portion washed with water, Sat. Na2CO3 and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the benzy alcohol which was used in the next step without further purification.
	With sodium tetrahydroborate; In methanol; at 0 - 20℃;	2-Hydroxybenzaldehyde (19.3 g) and benzyl bromide (25.9 g) were dissolved in N,N-dimethylformamide (50 mL). Cesium carbonate (59.0 g) was added to the solution at 0C, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with 1 mol/L aqueous sodium hydroxide solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 2-benzyloxybenzaldehyde. This compound was dissolved in methanol (100 mL). Sodium borohydride (5.73 g) was added to the solution at 0C, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with diethyl ether, and the organic layer was washed with 1 mol/L aqueous sodium hydroxide solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (32.4 g).1H-NMR (CDCl3) δ ppm: 2.28 (1H, t, J=6.6Hz), 4.74 (2H, d, J=6.6Hz), 5.13 (2H, s), 6.93-7.00 (2H, m), 7.23-7.45 (7H, m)
	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 2.5h;	To a solution of 2-benzyloxybenzaldehyde (2.0 g) in methanol (20 mL), NaBH4 (356 mg, 9.42 mmol) was added under ice cooling and stirred for 1 hour. After addition of additional NaBH4 (49 mg), the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated and water was added to the resulting residue, followed by extracting the mixture with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 2-benzyloxybenzyl alcohol (2.1 g) as a colorless oil. To a solution of 2-benzyloxybenzyl alcohol (2.1 g, 9.42 mmol) in tetrahydrofuran (10 mL), triethylamine (1.38 mL, 9.89 mmol) and methanesulfonyl chloride (0.766 mL, 9.89 mmol) were added under ice cooling and stirred at room temperature for 30 minutes. After filtration to remove the insoluble materials, the filtrate was concentrated to give (2-benzyloxyphenyl)methyl mesylate (3.24 g). To a suspension of methyl isobutyrylacetate (1.43 g, 9.89 mmol), sodium hydride (60% in oil; 396 mg, 9.89 mmol) and dimethoxyethane (10 mL), a solution of (2-benzyloxyphenyl)methyl mesylate (3.24 g) in dimethoxyethane (10 mL) was added and stirred at 70C overnight. After addition of 0.5 M HCl, the reaction mixture was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give an oil. To this oil, toluene (20 mL) and hydrazine monohydrate (317 mg, 9.89 mmol) were added and the resulting mixture was heated under reflux for 3 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The reaction mixture was concentrated and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 50:1 to 8:1) to give the titled compound (750 mg, 25%) as a light-yellow amorphous substance. 1H-NMR (200 MHz, CDCl3): δ 1.08 (d, J = 7.5Hz, 6H), 2.93 (quint, J = 7.5Hz, 1H), 3.75 (s, 2H), 5.12 (s, 2H), 6.82-6.95 (m, 2H), 7.09-7.19 (m, 2H), 7.31-7.50 (m, 5H). ESI m/z = 345(M+Na).
		Example 37; Ethyl 3-(4-[2-(benzyloxy)benzyl]oxy}-3,5-difluorophenyl)propanoate 2-(Benzyloxy)benzaldehyde (274 mg, 1.3 mmol) dissolved in methanol (20 mL), sodium borohydride (73 mg, 1.9 mmol) was added thereto, and then the mixture was stirred with ice cooling for 2 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 mL). Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (200 mg, 0.86 mmol), tributylphosphine (0.23 mL, 1.1 mmol) and azodicarbonyldipiperidine (282 mg, 1.1 mmol) were added thereto, and the mixture was stirred at room temperature for 12 hours. The reaction solution was purified with alumina column chromatography (ethyl acetate) and silica gel column chromatography (hexane/ethyl acetate = 100 : 0 to 80 : 20) to give the title compound (162 mg, yield 29%) as an oily matter.
	With sodium methylate; In methanol; N,N-dimethyl-formamide; at 120℃; for 15h;Inert atmosphere;	General procedure: To a solution of aldehyde/nitro compound (1 g) in dry DMF/xylene was added sodiummethoxide (10 equiv.) in methanol (5 ml). CuI (1 equiv.) was added whereverrequired. Reaction mixture was flushed by nitrogen, kept at 120oCfor appropriate time under nitrogen balloon andwater (100 ml) was added. It was extracted with ethyl acetate (3x75 ml) andcombined organic layer was dried over Na2SO4. Filtratewas concentrated under vacuum and the residue was further purified by columnchromatography in ethyl acetate/hexane as an eluent with appropriate polarityto get the product.
	With sodium tetrahydroborate; In tetrahydrofuran; at 0℃; for 1h;Inert atmosphere;	General procedure: Sodium borohydride (75.74 mmol) was added to a stirred solution of benzyl protected aldehyde (37.73 mmol) in 60 mL of THF at 0 oC. The reaction mixture was stirred vigorously for 1h. The reaction was quenched by dropwise addition of water at 0 oC. The aqueous layer was extracted with ethyl acetate (3 Χ 50 mL), and the organic layer was dried over anhydrous Na2SO4. After concentration under vacuum the crude product was chromatographed on silica gel (eluent =hexane/ethyl acetate, 9/1) to give 1 as colorless oil in good yield.
	With methanol; sodium tetrahydroborate; for 1h;Cooling with ice;	General procedure: To a solution of compound 7a (1.06 g, 10 mmol) in methanol(10 mL) was added NaBH4 (0.57 g, 15 mmol). After stirring for 1 hwhile cooled with an ice-water bath, methanol was evaporatedand the residue was dissolved in EtOAc (100 mL). The organic layerwas washed with water (3 100 mL) and brine (3 100 mL), anddried over MgSO4 overnight. EtOAc was evaporated to give 8a ascolorless oil (2.01 g, yield: 94%). ESI-MS m/z 109.4 [M+H]+. The crude product was used directly in the next reaction without furtherpurification. Compounds 8b-8u, 8aa-8ff, 10v-10w, 17a-17b and 22a-22hwere prepared using the same procedure described above

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 31 - 34.
[2]Tetrahedron Letters,2006,vol. 47,p. 5261 - 5264.
[3]Patent: US2008/293666,2008,A1 .Location in patent: Page/Page column 36.
[4]ARKIVOC,2010,vol. 2010,p. 27 - 40.
[5]Synthesis,2009,p. 4190 - 4202.
[6]Chemistry - A European Journal,2011,vol. 17,p. 2698 - 2703.
[7]Chemical Communications,2016,vol. 52,p. 8467 - 8470.
[8]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2846 - 2849.
[9]Phytochemistry,1998,vol. 48,p. 893 - 896.
[10]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1015 - 1022.
[11]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208.
[12]Patent: US5811459,1998,A .
[13]Patent: US6329376,2001,B1 .
[14]Patent: EP1400529,2004,A1 .Location in patent: Page 19.
[15]Patent: EP1609799,2005,A1 .Location in patent: Page/Page column 27-28.
[16]Patent: EP1688138,2006,A1 .Location in patent: Page/Page column 121.
[17]Tetrahedron Letters,2014,vol. 55,p. 155 - 162.
[18]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6816 - 6821.
[19]Russian Journal of Organic Chemistry,2015,vol. 51,p. 33 - 41.
Zh. Org. Khim.,2015,vol. 51,p. 40 - 47,8.
Zhurnal Organicheskoi Khimii,2015,vol. 51,p. 40 - 47,8.
[20]Chemistry - A European Journal,2016,vol. 22,p. 7959 - 7963.
[21]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3145 - 3157.

6
[ 3381-87-1 ]
HO-(2,6-naphthylidene)-C(NH)NHC(O)OCH₂-(p-C₆H₄)-OCH₂C(O)NHCH₂-(polystyrene resin) [ No CAS ]
6-(2-benzyloxy-benzyloxy)-naphthalene-2-carboxamidine [ No CAS ]

References: [1]Tetrahedron,1999,vol. 55,p. 6219 - 6230.

7
C₂₂H₂₂O₃ [ No CAS ]
[ 3381-87-1 ]

References: [1]Chemistry Letters,2000,p. 566 - 567.

8
[ 90-01-7 ]
[ 100-39-0 ]
[ 3381-87-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium chloride; In N-methyl-acetamide;	PREPARATION 1 2-Benzyloxybenzyltriphenylphosphonium chloride 151 g of potassium t-butoxide were added, whilst ice-cooling and stirring, to a solution of 152 g of salicyl alcohol in 600 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes; 160 ml of benzyl bromide were then added dropwise to the mixture. The reaction mixture was then stirred at a temperature of from 30 to 40 C. for 2 hours, after which it was partitioned between ethyl acetate and water. The organic layer was washed twice, each time with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was subjected to column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 228.5 g (yield 87%) of 2-benzyloxybenzyl alcohol as a colorless oil.
87.8%	In isopropyl alcohol;Heating / reflux;	13.78 g (80.5 mmol) of benzyl bromide, 10.00 g (80.5 mmol) of 2-hydroxybenzyl alcohol and 11.13 g (80.5 mmol) of potassium carbonate in 270 ml of 2-propanol are heated at reflux overnight. The suspension is cooled, taken up in ethyl acetate, washed with 1N aqueous sodium hydroxide solution and water, dried over magnesium sulfate and concentrated under reduced pressure.Yield: 15.15 g (87.8% of theory)Rf(SiO2, C4E1): 0.14

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2022 - 2031.
[2]Journal of Pharmacy and Pharmacology,2002,vol. 54,p. 349 - 364.
[3]Patent: US5556864,1996,A .
[4]Patent: US6864287,2005,B1 .Location in patent: Page/Page column 42.

9
[ 3381-87-1 ]
[ 14389-86-7 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 5261 - 5264.

10
[ 3381-87-1 ]
[ 5896-17-3 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 5261 - 5264.
[2]European Journal of Organic Chemistry,2018,vol. 2018,p. 5427 - 5434.

11
[ 3381-87-1 ]
[ 881672-54-4 ]