Nitric Acid → 2,4,5-Trifluoro-3-methyl-6-nitrobenzoic acid

Participants

Reaction Steps

A 43.4 g (0.21 mol) portion of 2,4,5-trifluoro-3-methylbenzoic acid was added to 120 ml of concentrated sulfuric acid under ice cooling. Thereto was added dropwise fuming nitric acid (d 1.52) in such a manner that the reaction temperature did not exceed 30° C. After completion of the dropwise addition, this was stirred for 1 hour at room temperature. After completion of the reaction, the reaction solution was poured into 1.5 liters of ice water to collect the formed crystals by filtration. The thus obtained crystals were washed with water (100 ml×3) and dissolved in 500 ml of ethyl acetate, and the solution was dried over anhydrous sodium sulfate. The filtrate obtained above was extracted with chloroform (300 ml×4) and dried over anhydrous sodium sulfate. Thereafter, the organic layers were combined and concentrated to yield 50.3 g (quantitative) of the title compound.

Provenance & Evidence