Hydrochloric Acid → 4-Chloro-2-nitrobenzoyl chloride

Participants

Reaction Conditions

Reaction Steps

A mixture containing 1200 g. (5.95 moles) of 4-chloro-2-nitrobenzoic acid, 5000 ml. (69 moles) of thionyl chloride and 40 ml. of N,N-dimethylformamide was stirred 4 hours while the temperature was maintained at 26° C. When the evolution of hydrogen chloride subsided, the temperature was raised to 65° C. and stirring was continued an additional hour. After removing excess thionyl chloride by vacuum distillation, the residue was dissolved in 1 l. of 1,2-dichloroethane and the solution was evaporated under reduced pressure. The residue which was essentially free of thionyl chloride was dissolved in 5 l. of 1,2-dichloroethane and the solution was twice treated with decolorizing carbon and filtered to give a final solution of 4-chloro-2-nitrobenzoyl chloride in 1,2-dichloroethane which was used directly in the next step.

Provenance & Evidence