P-Toluic Acid → Methyl 4-methylbenzoate

Participants

Reaction Steps

To a solution of p-toluic acid (175 g, 1.28 mol) in methanol (2 L) was added dropwise thionylchloride (612 g, 5.14 mol) under stiring at 5° C. The mixture was refluxed overnight, then the solvent evaporated. The residue obtained was treated with a 10% aqueous NaHCO3 solution (pH˜8) The product was extracted with ethyl acetate, washed-with water and dried. The solvent was removed and the crude was purified by column chromatography (pet ether/ethyl acetate) to give methyl-p-toluate as colorless liquid (180 g, 93%).

Provenance & Evidence