Nitric Acid → (2-Nitro-4-trifluorobenzyl)acetic acid

Participants

Reaction Steps

To a cooled (0°) solution of 4-trifluoromethylphenylacetic acid (550 g; 1.45 mol) in sulfuric acid (2.0 L) was added, over 1.5 hours, nitric acid (90%; 300 mL) at such a rate as to maintain the temperature between 0° and 5° C. The solution was stirred for 15 minutes, then poured into ice water (17 L). The solid that separated was collected on a filter, washed with water (2 times with 2.5 L, by resuspension), then dissolved in ether (3.0 L). The ethereal solution was washed with water (2 times with 1.0 L), dried, then concentrated in vacuo. The last traces of water were removed by co-distillation with ethanol (500 mL). Yield: 588.2 g (96.4%). The material was suitable for further transformation. Additional product (116.6 g) was obtained from a scouting run.

Provenance & Evidence