Hydrochloric Acid → HCID 18977936, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (14.5 g) in water was added to a stirred, cooled suspension of 3-amino-4-methylbenzoic acid (30.23 g) in a mixture of acetic acid and concentrated hydrochloric acid at a temperature between 0° C. and 5° C. The mixture was stirred at 0°-5° C. for 1 hour and the resulting mixture was added to a stirred mixture of dimethyl disulphide (22 ml) and copper powder (0.25 g) in acetic acid while maintaining the temperature at about 35° C. Further copper powder (3 g) was added during the reaction in order to maintain the gas evolution. It was stirred for a further 1 hour then poured into water and the solid filtered off. It was treated with a mixture of ethyl acetate and cyclohexane, heated and the insoluble material was filtered off to give 4-methyl-3-methylsulphenylbenzoic acid (19.5 g) as a white solid, m.p. 174.6°-175.2° C.

Provenance & Evidence