Preparation of acetanilide

Preparation of acetanilide

100 g aniline and 150 g acetic acid are mixed in a round flask of one-litre capacity, fitted with an aircondenser, and boiled 10 to 12 hours. The tube forming the air-condenser should not be too long, in
order that the water vapor may escape while the aniline and acetic acid are condensed. The hot
reaction mixture is poured into hot water containing 30 g of concentrated hydrochloric acid. After
cooling, the crude acetanilide is filtered washed with distilled water. The filtrate contains about 2030 grams of aniline hydrochloride, which, could be regenerated. The acetanilide is dried at 110120 C. The yield of acetanilide is 220-250 g. Acetanilide is purified by crystallization from hoe water
forms white leafy crystals melting at 115 C, boiling at 295 C. By boiling with concentrated
hydrochloric acid, acetanilide is hydrolyzed to aniline and acetic acid.

Hydrolysis of acetanilide