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), and water (449.2 g) was placed in a 1 l-flask. The mixture was heated to 82° C., and triethylamine was added thereto so as to adjust the pH of the mixture at 9.0-9.3. Six hours after the reaction started, liquid chromatographic analysis revealed that the reaction mixture contained 67.6 g of p-cyanobenzoic acid (yield 92%). 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 so that the mixture dissolves. The resultant mixture was cooled for crystallization, to thereby obtain 62.4 g of p-cyanobenzoic acid crystal (purity 97.8%, yield 83%).

Provenance & Evidence