Acetanilide → N-[4-(1-oxopropyl)phenyl]acetamide

Participants

Reaction Conditions

Reaction Steps

1290 g of aluminium chloride (9.6 mole) were suspended with stirring in 1500 ml of carbon disulphide. 405 g of acetanilide (3 moles) were added slowly to this suspension, while the temperature was kept at 25° C. The reaction mixture was heated until reflux and was cooled immediately to 25° C. 565 ml of propionyl chloride (6.5 moles) were added dropwise in such a way that the temperature was kept at 25° C. The reaction mixture was heated until reflux for 5 hours and kept overnight at ambient temperature (20° C.). The supernatant carbon disulphide layer was decanted and the remaining viscous mixture was poured in a mixture of ice and hydrochloric acid. The residue formed was filtered off and further recrystallized from a mixture of 1500 ml of ethanol and 75 ml of water. Drying was applied under vacuum at 100° C. A light yellow powder was obtained.

Provenance & Evidence