2-(2-phenylmethoxyphenyl)ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl (2-benzyloxyphenyl)acetate (935 mg) in tetrahydrofuran (9.4 ml) was added sodium borohydride (600 mg) and the suspension was heated to 45° C. A mixture of methanol (3 ml) and tetrahydrofuran (6 ml) was added dropwise to the mixture and the mixture was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and quenched by 1 N aqueous hydrochloric acid solution. The organic layer was washed with brine, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)] to afford 2-(2-benzyloxyphenyl)ethanol (764 mg). was added dropwise to the mixture The reaction mixture was concentrated under reduced pressure The residue was dissolved in dichloromethane quenched by 1 N aqueous hydrochloric acid solution The organic layer was washed with brine dried evaporated under reduced pressure The residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)]

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g). the mixture was refluxed under heating for 2 hours The solvent was distilled away under reduced pressure, water was added the mixture was extracted with ethyl acetate The organic layer was washed with a 2M aqueous potassium hydroxide solution a saturated brine and dried over sodium sulfate The solvent was distilled away under reduced pressure