Chlorine → 4-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

Participants

Reaction Steps

A solution of 16.75 g of 4-chlorobenzaldoxime in 155 ml of chloroform was cooled to 5°. Chlorine gas was passed slowly through the solution until no more was absorbed; a blue-green color developed and the temperature slowly increased to 20°. The mixture was stirred for 1 hour at 5°, then heated under reflux for half an hour. The mixture was cooled to room temperature, then the solvent was evaporated under reduced pressure to give a white solid. The solid was collected and dried in a vacuum desiccator in a refrigerator at 5° to give 20.4 g of 4-chlorobenzohydroximoyl chloride, m.p. 81°-85°.

Provenance & Evidence