Benzoic Acid → Benzoyl chloride

Participants

Reaction Steps

An amount of 500 g of benzoic acid was dissolved in 2000 ml of acetone, and 400 g of thionyl chloride was added dropwise over 3 hours. Thereafter, the mixture was stirred at a room temperature overnight under reflux. The solvent and unreacted thionyl chloride were removed to give 231 g of benzoyl chloride. Subsequently, the thus obtained benzoyl chloride was dissolved in 2000 ml of acetone and decompressed to 25 mmHg with an aspirator in a cooled state at 5° C. or less, and thereafter ammonia gas was purged therein. The reaction was stopped when the reaction system returned to normal pressure, and the reaction mixture was filtered under reduced pressure to obtain 169 g of ammonium benzoate. After the ammonium benzoate was washed with 1000 ml of water and then dissolved in 1N aqueous ice-cooled sodium hydroxide solution, bromine was added thereto. Thereby, the hydrolysis and decarboxylation was caused through the Hoffmann rearrangement to give the target 10.9 g of aniline.

Provenance & Evidence