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 (25.145 g, 161 mmol) and N,N-dimethylacetamide (0.752 mL, 8.03 mmol). The mixture was heated to 55 to 60° C. and then thionyl chloride (12.30 mL, 169 mmol) was added over 1 h at <62° C. The reaction mixture was stirred at 58 to 62° C. for 2 h and then allowed to cool to <30° C. to give the title compound as a dark brown solution (29.730 g) containing N,N-dimethylacetamide and thionyl chloride. This was transferred to an addition funnel using toluene (5 mL).

Provenance & Evidence