4-Nitrobenzoic Acid → 4-Nitrobenzoyl chloride

Participants

Reaction Steps

A mixture of p-nitrobenzoic acid (500 g, 3.0 moles, 1 equiv) and thionyl chloride (600 mL, 8.2 moles, 2.73 equiv) was heated to reflux for 6-7 hours until a clear solution was obtained. Excess of thionyl chloride was removed by distillation followed by co-distillation with toluene (300 mL). The reaction mass was cooled to room temperature, and hexane (1.5 L) was added, forming a precipitate, which was then filtered and dried under vacuum, yielding 4-nitrobenzoyl chloride as a yellow solid (530 g, approximately 100% yield), which was used without any further purification.

Provenance & Evidence