Nitric Acid → 5-Chloro-2-methyl-3-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 5-chloro-2-methylbenzoic acid (9.9 g, 58 mmol) in concentrated H2SO4 (70 ml, 1310 mmol) was cooled to −5° C. in an acetone/ice bath. A mixture of concentrated nitric acid (4.9 ml, 75 mmol) and concentrated H2SO4 (5.0 ml, 94 mmol) was added dropwise to the reaction mixture at −5° C. over 30 minutes. The reaction mixture was stirred at −5° C. for 2 hours before being poured onto ice (150 g) and the precipitate collected by filtration. The precipitate was dissolved in EtOAc (100 ml) and washed with brine (100 ml) before being dried over MgSO4, filtered and concentrated under reduced pressure to give 11.9 g of the title compound as an off-white solid. This material was used without further purification. LC-MS 57%, m/z=214.0/216.0, 1H NMR (500 MHz, Chloroform-d) δ 10.37 (1H, br. s.), 8.19 (1H, d, J=2.21 Hz), 7.91 (1H, d, J=2.21 Hz), 2.67 (2H, s).

Provenance & Evidence