Thionyl Chloride → 2-(4-Chlorophenyl)ethyl chloride

Participants

Reaction Conditions

Reaction Steps

A 10-liter jacketed reactor equipped with an overhead stirrer, a thermocouple, an addition funnel, and a dry ice/acetone condenser was charged with 2-(4-chlorophenyl)ethanol (2005 g, 12.8 mol) and swept with nitrogen. DMF (49.6 mL, 640 mmol) was charged to the reactor and the reactor contents were heated to 60° C. Thionyl chloride (1607.3 g) was added at a rate sufficient to maintain the temperature at >49° C. and <70° C. On completion of the addition, the reaction was held at 52.6° C. (jacket temperature). It was then cooled to 20° C. and allowed to stir at room temperature overnight. The reaction mixture was concentrated at 22 torr and 60° C. (water bath) for 1.5 h, to leave 1-chloro-4-(2-chloroethyl)benzene (2256 g).

Provenance & Evidence