Nitric Acid → HCID 69650076, compound

Participants

Reaction Steps

A solution of 2-chlorophenylacetic acid (10.0 g, 58.6 mmol) in concentrated sulfuric acid (40 mL) was cooled to −10° C. and slowly reacted with a solution of fuming nitric acid (2.80 mL, 66.7 mmol) in concentrated sulfuric acid (7.2 mL). After 2.5 hours the reaction was slowly poured over ice water (400 mL), filtered over a coarse filter frit, washed once with cold water, and dried on the frit overnight giving the title compound (13.5 g, 98%) as a white solid. Integration of the proton NMR spectrum showed the product contained about 0.2 equivalents of 2-chlorophenylacetic acid, but thin-layer chromatography showed this to be inseparable from the product. 1H NMR (300 MHz, CDCl3/CD3OD) δ 8.25 (d, 1H, J=2.7 z), 8.13 (dd, 1H, J=8.7 Hz, 2.7 Hz), 7.61 (d, 1H, J=8.8 Hz), 3.89 (s, 2H).

Provenance & Evidence