Dimethylformamide → 5-Acetyl-2-methylbenzene-1-sulfonyl chloride

Participants

Reaction Steps

363 Grams (1.0M) of N,N-diethylaniline salt of 5-acetyl-2-methylbenzenesulfonic acid was dissolved in 934 g of chloroform, to this solution was added a mixture of 80.3 g (1.1M) of N,N-dimethylformamide with 130.9 g (1.1M) of thionyl chloride at a temperature of 2°-3° C., and the whole mixture was stirred at the same temperature for 1 hour. 1,500 Grams of water was added to this reaction mixture, the chloroform layer was separated and washed 3 times with 500 g of water. The chloroform layer was concentrated to obtain 203.1 g (0.874M) of 5-acetyl-2-methylbenzenesulfonyl chloride. The yield was 87.4% on the basis of N,N-diethylaniline salt of 5-acetyl-2-methylbenzenesulfonate.

Provenance & Evidence