Ethanol → 3-HYDROXY-4-METHYLBENZOIC ACID ETHYL ESTER

Participants

Reaction Steps

A mixture of 3-hydroxy-4-methylbenzoic acid (25.42 g, 167 mmol, TCl US) and concentrated sulfuric acid (3 mL) in absolute ethanol (180 mL) was heated at reflux for 20 hours. After cooling, solid sodium bicarbonate (10 g) was added to neutralize the acid. The mixture was partitioned between diethyl ether (2×400 mL) and water (2×300 mL). The organic layers were washed with brine (300 mL), combined, dried (MgSO4), filtered, and concentrated. The residue was recrystallized from hexanes to give 3-hydroxy-4-methyl-benzoic acid ethyl ester as white crystals in two crops. (Yield 29.14 g).

Provenance & Evidence