Hydrochloric Acid → HCID 15114333, compound

Participants

Reaction Steps

A solution of the 4-ethylsulfonyl-2,3-dichlorobenzoic acid prepared in Example 3 (0.2 mole), ethyl mercaptan (0.8 mole), sodium hydroxide (1 mole) in water (300 ml) was heated at reflux for 24 hours. After cooling, the reaction mixture was acidified with concentrated hydrochloric acid and extracted with methylene chloride. The layers were separated, and the methylene chloride layer was dried over magnesium sulfate. Evaporation of the methylene chloride in vacuo then afforded a mixture of the acids which were esterified to the methyl esters with methanol and sulfuric acid in ethylene dichloride by the procedure of Clinton and Lawkowski, J. Amer. Chem. Soc., 70, 3135 (1948). The esters were then separated via standard chromatographic techniques. Basic hydrolysis of each methyl ester then afforded the 3,4-bis-ethylthio-2-chlorobenzoic acid, m.p. 73°-75° C. and 2-chloro-4-ethylsulfonyl-3-ethylthio-benzoic acid oil.

Provenance & Evidence