Potassium Nitrate → 6-Chloro-2-methyl-3-nitrobenzoic acid

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Reaction Steps

2-Chloro-6-methylbenzoic acid (99 mg, 0.58 mmol) was dissolved in conc. hydrochloric acid (1 mL) and cooled in an ice bath. To this solution potassium nitrate in conc. hydrochloric acid (1 mL) was added drop wise. The reaction mixture was stirred for 5 min, then the ice bath was removed and stirring was continued for another 2 hours. The reaction mixture was poured onto ice (25 g) and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo to give a mixture of the desired 3-nitro (70%) and the 5-nitro (30%) derivatives (118.6 mg, 95%). No effort was made to separate the two isomers, and the mixture was used in the next step.

Provenance & Evidence