m-Chloroperbenzoic acid → 2-(Benzyloxy)biphenyl-3-ol

Participants

Reaction Steps

A solution of 2-(benzyloxy)biphenyl-3-carbaldehyde (14.4 g, 50 mmol) in dichloromethane (250 mL) was stirred on an ice bath and m-chloroperbenzoic acid (70%, 13 g) was added in portions over 20 min. Stirring was continued overnight at room temperature. The reaction mixture was diluted with dichloromethane (to 600 mL) and washed with saturated sodium bicarbonate (2×300 mL) and water (300 mL). The organic layer was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator. The residue was taken in methanol (250 mL), potassium hydroxide (5 g) was added and this mixture was stirred at room temperature for 2 hr. The solvent was removed in a rotary evaporator. The residue was taken in water (200 mL) and made acidic with 6N hydrochloric acid. The aqueous phase was extracted with ethyl acetate (450 mL). The organic extract was washed with water (100 mL), dried over sodium sulfate and the solvent was removed in a rotary evaporator. The crude product was purified by chromatography on silica (360 g) with 10% ethyl acetate in heptane (4 L) to afford 30 (12 g, 87%).

Provenance & Evidence