Water → 3-Phenoxybenzyl alcohol

Participants

Reaction Steps

After stirring the reaction mixture for an additional 0.5 hour at 0°-5°C, a solution of 3860 grams (18 moles) of m-phenoxybenzoic acid in tetrahydrofuran was added dropwise over a 4 hour period while maintaining a reaction temperature of 0°-10°C. When the addition was complete, the reaction mixture was stirred for 12 hours at 20°C followed by 2 hours at 40°C. The reaction mixture was then transferred to a 10 gallon bottle containing 6 liters of water and 8 liters of diethyl ether. After mixing thoroughly, the aqueous layer was removed and the organic layer was extracted with water (1 × 4 liters), extracted with aqueous saturated sodium bicarbonate solution (1 × 4 liters), extracted with aqueous saturated sodium chloride solution (1 × 4 liters), dried over anhydrous potassium carbonate, filtered, and concentrated on a rotary evaporator. Short-path distillation gave 3000 grams (83% yield) of m-phenoxybenzyl alcohol, bp 135°-140°C/0.10 mm, n20D 1.5935.

Provenance & Evidence