Methanol → Methyl 4-methyl-3-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methyl-3-nitrobenzoic acid (27.95 g, 154 mmol) in MeOH (550 mL) was treated with concentrated H2SO4 (10 mL, 188 mmol) and heated to reflux for 17 hours. The reaction was cooled and concentrated under reduced pressure. EtOAc (300 mL) and brine (400 mL) were added and the solution cooled to 0° C. 10N NaOH solution (40 mL) was slowly added until the acid content was neutralized and the solution basic. The organic phase was separated and the aqueous was then extracted with EtOAc (2×400 mL), and the combined organic phases dried (MgSO4), filtered, and concentrated under reduced pressure to give 4—Methyl-3-nitrobenzoic acid methyl ester as a white solid (29.37 g, 98%).

Provenance & Evidence