Benzyl Alcohol → 1-Benzyloxy-3-chloro-2-propanol

Participants

Reaction Conditions

Reaction Steps

A 1,000 mL, 3-necked flask equipped with a mechanical stirrer, condenser, thermometer and 500 mL addition funnel was charged with benzyl alcohol (324 g, 3.0 mol) and 5% BF3 -etherate in ether (10 mL). This mixture was stirred and heated to 80° C. Epichlorohydrin (278 g, 3.0 mol) was added dropwise over 6 hours, and the reaction mixture was stirred an additional 24 hours at 80° C. The crude product was distilled from NaHCO3 (1 g) using a 25 cm Vigreux column. The fractions boiling from 95° C. (0.05 mm) to 120° C. (0.03 mm) were collected and combined to yield 353 g (58%) of pure 3-benzyloxy-2-hydroxypropyl chloride.

Provenance & Evidence