Acetic Acid → 3-(2-Hydroxy-4-methylbenzoyl)benzoic acid

Participants

Reaction Steps

A mixture of 3-(2-hydroxy-4-methylbenzoyl)benzonitrile (5.78 g; see Example 29), acetic acid (48 g), and a solution of 75% sulfuric acid (48 g) is refluxed for 3 hours. The resulting mixture is diluted with water (100 ml) and extracted with ether (3×75 ml) followed by methylene chloride (2×75 ml). The combined extracts are dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on silica gel (methylene chloride then hexanes:ether:acetic acid; 50:50:1). The resulting yellow solid is recrystallized from ligroin/isopropyl ether to yield 3-(2-hydroxy-4-methylbenzoyl)benzoic acid (3.62 g), m.p. 198°-215° C.

Provenance & Evidence