Chloroacetic Acid → 1,3-Dimethyl-5-(methylsulfonyl)benzene

Participants

Reaction Conditions

Reaction Steps

To a stirring slurry of 3.2 g (25.4 mmol) of Na2SO3 and 6.2 g (73.8 mmol) of NaHCO3 in 20 mL of H2O at 75° C. was added 5.0 g (24.4 mmol) of 3,5-dimethylbenzene-1-sulfonyl chloride in several portions. After 2 h at 75° C., 3.5 g (37.0 mmol) of chloroacetic acid was added in portions followed by 1.5 g (37.5 mmol) of NaOH in 3 mL of H2O. The mixture was stirred at 135° C. for 13 h, and 3 N HCl was added to a pH=1. A colorless precipitate formed, and the mixture was filtered through a Buchner funnel to provide 3.8 g of 1,3-dimethyl-5-(methylsulfonyl)benzene in 84% yield.

Provenance & Evidence