Methanol → [3-(Benzyloxy)-4-methylphenyl]methanol

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:15]=[CH:16][C:17]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Versuchsvorschrift

To a solution of 3-(benzyloxy)-4-methylbenzoic acid (2.80 g) in THF (10 mL) was added dropwise a 1.0 M solution of borane-THF complex in THF (23 mL) at room temperature over 30 min, and the mixture was stirred for 2 hr. Methanol (20 mL) was added dropwise to the reaction mixture over 20 min, and water was further added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.60 g) as a yellow oil. This compound was used for the next step without further purification.