Methanol → 4-Cyanobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture containing ethyl p-cyanobenzoate (87.5 g, 0.5 mol), methanol (192.5 g), water (449.2 g) was placed in a 1 l-flask. The mixture was heated to 80° C. with stirring. A 20% aqueous solution of sodium hydroxide was added to the mixture so as to adjust the pH of the mixture at 8.0-8.3. Eighteen hours after the reaction started, liquid chromatographic analysis revealed that the reaction mixture contained 64.7 g of p-cyanobenzoic acid (yield 88%). The reaction mixture was cooled to 30° C., and hydrochloric acid was added thereto to lower the pH to 3.1. The mixture was heated again to 82° C., and methanol was added thereto until the mixture dissolves. The resultant mixture was cooled for crystallization, to thereby obtain 64.6 g of p-cyanobenzoic acid crystal (purity 96.7%, yield 85%).

Provenance & Evidence