Nitric Acid → 2-(2-Chloro-5-nitrophenyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-chlorophenyl)acetic acid (15 g, 88 mmol) in cone. H2SO4 (100 mL) was cooled to −20° C. and treated (drop wise) with cone. HNO3 (9.4 g, 97 mmol). The resulting mixture was stirred at −20° C. for an additional 30 min. The reaction mixture was poured into the ice-water, and the mixture was extracted with EtOAc (3×200 mL), the combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo to give (2-chloro-5-nitrophenyl)acetic acid (15 g, 79% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.58 (s, 1 H), 8.35 (m, 1 H), 7.96 (m, 1 H), 4.12 (s, 2 H).

Provenance & Evidence