Methanol → Methyl 4-methyl-3,5-dinitrobenzoate

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Reaction Steps

To a mixture of 4-methyl-3,5-dinitro-benzoic acid (3) (35.1 g, 155 mmol) in anhydrous methanol (250 mL) is slowly added thionyl chloride (4 mL, 54 mmol). The resulting solution is heated to reflux for 16 hours. The solution is cooled to room temperature and then further cooled in an ice-water bath. The solid that forms is filtered and dried to give 4-methyl-3,5-dinitro-benzoic acid, methyl ester (32) (33.5 g, 139.5 mmol, 90% yield), as a white crystalline solid.

Provenance & Evidence