Acetic Acid → 4-Methoxy-2-nitrobenzoic acid

Participants

Reaction Steps

4-Cyano-3-nitroanisole (52.3 g., 0.294 mole) was slowly added to a cooled solution of 53 ml. each of acetic acid, water and sulfuric acid. The solution was refluxed for 5 hours, and then diluted with 160 ml. water. After cooling, the resulting solid was filtered and dissolved in 10% sodium hydroxide solution. After decolorization with charcoal the solution was acidified with 6 N HCl, cooled and the yellow product (51.0 g., 88% yield) was filtered. An analytical sample was recrystallized from methanol/water, M.P. 196°-7° C.

Provenance & Evidence