Hydrochloric Acid → (4-Phenoxyphenyl)methanol

Participants

Reaction Steps

To a solution of 4-(phenyloxy)benzoic acid (10.4 g, 48.7 mmol) in tetrahydrofuran (30 ml) was added 1M tetrahydrofuran solution of borane (63 ml, 63 mmol) at room temperature and the mixture was stirred overnight. 1N Hydrochloric acid was added to the reaction solution for quenching and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from hexane to give (4-(phenyloxy)phenyl)methanol (8.51 g, 87%).

Provenance & Evidence