Hydrochloric Acid → 5-Methyl-2-(phenylsulfanyl)benzoic acid

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Reaction Steps

To a solution of 855 g of potassium hydroxide in 7 litres of water are added, at 50° C under argon, 420 g of thiophenol and the mixture is stirred for 15 minutes. There are then added thereto 22.1 g of copper powder and 1 kg of 2-iodo-5--methyl-benzoic acid and the mixture is heated for 7 hours under reflux. After cooling, the mixture is adjusted to pH 3 with 600 ml of concentrated hydrochloric acid and extracted with methylene chloride, washed with water, dried over sodium sulphate and concentrated to a thick crystal mash. This is filtered under suction, washed with cold ethanol and low--boiling petroleum ether and dried. Thee is obtained 3--methyl-6-(phenylthio)-benzoic acid of melting point 156°-157° C.

Provenance & Evidence