Methanol → Methyl 4-bromo-2-methylbenzoate

Participants

Reaction Steps

Reflux a mixture of 54.30 gm. (0.252 mole) of 5-bromo-o-toluic acid, 400 ml. of methanol and 5 ml. of concentrated sulfuric acid for 18.5 hours. Remove the methanol under vacuum. Dissolve the residue in benzene, wash with water, aqueous sodium bicarbonate solution, water and dry over anhydrous magnesium sulfate. Remove the solvent under vacuum and distill the residual oil to obtain the title product together with the 3-bromo isomer as a colorless oil (yield 41.6 gm., b.p. 132°-135° C./0.1 mm). Chill the oil in a refrigerator for 1 hour and separate the solids to obtain 12.53 gm. of white solid (m.p. 42°-46° C., mainly the 5-bromo isomer).

Provenance & Evidence