4-Nitrobenzoic Acid → 4-Nitrobenzoyl chloride

Participants

Reaction Conditions

Reaction Steps

4-Nitrobenzoic acid, thionyl chloride and DMF were placed in a 3-liter 4-necked glass flask and heated for 2 hours at 78° C. under reflux. The end of the reaction was monitored by the clarity of the reaction mixture. There was a clear solution at the end of the reaction. Thionyl chloride was removed under reduced pressure. Dichloroethane (1 liter) was added, and evaporation was carried out to yield 4-nitrobenzoyl chloride in the form of a solid. The solid was dissolved in dichloroethane (1 liter). Dichloroethane (10 liters) was introduced into a 20-liter glass flask and cooled to 0° C. Aluminium chloride was added at 0-5° C. The 4-nitrobenzoyl chloride prepared above, dissolved in dichloroethane, was then added dropwise at 0-5° C. Phenoxypropionic acid was added in portions to the reaction composition at 0.5° C., and stirring was carried out overnight at 25° C. The TLC was checked and the reaction composition was quenched in a mixture of hexane (8 liters) and ice-water (15 liters). The composition was stirred and the solids were filtered off. The product was washed with hexane and dried.

Provenance & Evidence