3-Phenoxybenzyl chloride → Benzenemethanol, 3-phenoxy-, 1-acetate

Participants

Reaction Steps

m-Phenoxybenzyl chloride (218.5 g; 1 mole), sodium acetate (205 g; 2.5 mole), tetrabutylammonium bromide (10.9 g; 0.034 mole) and water (327 ml) were heated and stirred under reflux for 2 hours. On cooling m-Phenoxybenzyl acetate (241.5 g; 99.8% yield) separated as the upper layer. Its purity was 99%. m-Phenoxybenzyl acetate (242 g; 1 mole), sodium hydroxide (80 g; 2 mole), tetrabutylammonium bromide (12 g; 0.037 mole) and water (240 ml) were stirred at ambient temperature for 4 hours. The upper organic layer was dissolved in toluene (400 ml). The resulting solution was washed with water (2×200 ml) and treated with ion-exchange resin (Zerolit 236) and charcoal. Evaporation of the toluene gave the alcohol with a purity of 98.9% by gas chromatography (198 g, 99% yield).

Provenance & Evidence