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 a caustic scrubber, was charged 2-(4-chlorophenyl)ethanol (25.033 g, 160 mmol). N,N-Dimethylacetamide (0.749 mL, 7.99 mmol) was added and the mixture was heated in oil bath to 58° C. Thionyl Chloride (12.25 mL, 168 mmol) was charged over 1 h while the reaction temperature was maintained at <66° C. The resulting brown solution was stirred at 60 to 64° C. for 2.5 h and then allowed to gradually cool to room temperature leaving a dark brown oil.

Provenance & Evidence