2-Methyl-3-nitrobenzoic acid → Ethyl 3-(2-methyl-3-nitrophenyl)-3-oxopropionate

Participants

Reaction Steps

A solution of 2-methyl-3-nitrobenzoic acid (10.0 g, 55.2 mmol) and carbonyldiimidazole (13.4 g, 82.8 mmol) in tetrahydrofuran (200 mL) is stirred at room temperature for 2 hours under an argon atmosphere. The magnesium salt of malonic acid monoethyl ester (47.4 g, 165 mmol) is added and the reaction mixture is heated at reflux for 18 hours. The reaction mixture is quenched with water (200 mL) and acidified to pH=1 with concentrated HCl. The product is extracted into ethyl acetate and washed with 1.0 N HCl, saturated aqueous sodium bicarbonate, and brine. The organic layer is dried over magnesium sulfate and evaporated. Recrystallization of the residue gives ethyl 2-methyl-3-nitro-β-oxobenzenepropanoate (10.6 g, 76%), mp=50-51° C.

Provenance & Evidence