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

Participants

Reaction Conditions

Reaction Steps

Into a 250-mL round-bottom flask equipped with magnetic stirring, a thermocouple, a condenser, and a nitrogen bubbler vented to caustic scrubber, was charged 2-(4-chlorophenyl)ethanol (25.119 g, 160 mmol), toluene (73 mL) and N,N-dimethylacetamide (0.751 ml, 8.02 mmol). The mixture was heated in oil bath to between 65 and 70° C. and thionyl chloride (12.29 ml, 168 mmol) was charged over 1 h with a maximum reaction temperature of 69° C. The reaction was then stirred for 2 h at 65 to 70° C. The resulting dark-brown solution was cooled to 40° C. and washed with water (2×40 mL) by stirring for 2-5 min at 45° C. (bath) and separating the phases at room temperature. The organic phase was further washed with saturated aqueous sodium bicarbonate solution (3×40 mL) by stirring for 2-5 min at 50° C. (bath) and separating the phases at room temperature.

Provenance & Evidence