Hydrochloric Acid → 2-Chloro-3-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

Sodium nitrite (14.0 g; 0.2 mol) was added to a solution of 2-amino-3-methylbenzoic acid (30.2 g; 0.2 mol) in a mixture of water (200 mL) and NaOH/aq (30%; 24 mL). The solution was cooled to 0° C. and was added dropwise, with stirring, to a mixture of HCl (conc.; 87.6 mL) and ice (100 g). After stirring for a few minutes, the resultant solution was added to an ice cold mixture of HCl/aq (23%; 100 g), CuCl (20 g; 0.2 mol) and water (40 mL). The solution was stirred at room temperature for 30 minutes and at 100° C. for 30 minutes, cooled, and the resultant precipitate was isolated by filtration, was washed with water, and was dried overnight, yielding 27.4 g (80.3%) of a white crystalline material.

Provenance & Evidence