Acetic Acid → 3-Cyclopentyloxy-4-(methylthio)benzoic acid

Participants

Reaction Steps

A solution of methyl 3-cyclopentyloxy-4-(methylthio)benzoate (24.3 g, 91.4 mmol) in water (200 mL) and ethanol (50 mL) containing sodium hydroxide (18.3 g, 460 mmol) is heated under reflux for 3 hours. The solution is then poured into water (750 mL) and 1N acetic acid is added dropwise with stirring to between pH 5-6. The solid which separates is collected by filtration, washed with water (4×100 mL) and dried giving 3-cyclopentyloxy-4-(methylthio)benzoic acid (21.1 g, 91.7%) as a cream solid m.p. 158-160° C. [Elemental analysis: C,61.5; H,6.31%; calculated: C,61.88; H,6 39%]

Provenance & Evidence