Nitric Acid → 4-Nitro-1,2-benzenediacetic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1,2-phenylenediacetic acid (10.2 g, 52.5 mmol) in conc. sulfuric acid (33 mL), cooled to −10° C., is added over 10 min a mixture of nitric acid (3.9 mL) and sulfuric acid (1.3 mL). After stirring at −10° C. for 4 h, the reaction mixture is poured onto ice (250 cc). The resulting mixture is extracted with ethyl acetate (3×300 mL). The combined organic phases are washed with H2O (100 mL), dried (MgSO4), filtered and concentrated to afford a white solid. The solid is recrystallized from methyl-tert-butyl ether in hexane to give 8.2 g (34.3 mmol, 65%) of the desired product. mp 187-188° C.

Provenance & Evidence