Methanol → (3-Benzyloxy-2-methyl-phenyl)-methanol
Reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([CH3:18])=[C:11]([CH2:12][OH:13])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(benzyloxy)-2-methylbenzoic acid (800 mg) in THF (10 mL) was added dropwise a 1.0 M solution of borane-THF complex in THF (6.6 mL) at room temperature over 30 min, and the mixture was stirred at room temperature for 2 hr. Methanol (10 mL) was added to the reaction mixture under ice-cooling, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (480 mg) as a white solid.