Reaction with hydrogen sulfide and its derivatives

Reaction of alcohols with sulfur compounds a. With hydrogen sulfide and its derivatives 

Alcoholic hydroxyl groups are replaced when treated with thiols, water being split off and organic sulfides formed. Thus, for example, (desylthio)-acetic acid is obtained from benzoin and mercaptoacetic acid 369 

C6H5COCH(C6H5)OH +HSCH2COOH C6H5COCH(C6H5)—s—ch2cooh + h2o 

Benzoin (5 g) and mercaptoacetic acid (6.5 g) are warmed for 0.5 h on a water-bath while hydrogen chloride is passed in. The mixture is then treated with cold sodium carbonate 

Kaufmann, Angew. Chem., 54, 195 (1941) Neuere Methoden der praparativen organischen Chemie, Verlag Chemie, Berlin, 1944, p. 237. 

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