Nitric Acid → 2-Nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid

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Reaction Steps

To a solution of 63.2 g (0.20 mole) of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid in 160 ml of concentrated sulfuric acid is added 40 ml of fuming nitric acid (90%) dropwise with stirring at 0°-5°. Following the nitric acid addition the solution is allowed to warm to 20° with stirring over a 1-hour period. The solutionis then added to a mixture of ice and water and allowed to stand for 18 hours. A precipitate results and is filtered, washed with water and dissolved in ether to obtain a solution which is washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated to give a residual solid. The residual solid is recrystallized from chlorobutane to give 40 g of 2-nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid having a melting point of 115°-116°.

Provenance & Evidence