Sulfuric Acid → Methyl indane-2-carboxylate

Participants

Reaction Steps

A solution of 50 g. of indan-2-carboxylic acid (prepared according to the procedure reported by E. D. Bergmann and E. Hoffman, J. Org. Chem., 26, 3555 (1961)) and 5 ml. of con d sulfuric acid in 500 ml. of methanol is heated at reflux for 3.0 hours then is cooled in ice. The cooled solution is neutralized (pH~5) with saturated sodium bicarbonate, is concentrated, and the aqueous layer is extracted with methylene chloride. The combined organic extracts are washed with saturated bicarbonate, with saturated brine, are dried (anhydrous magnesium sulfate), and are concentrated. Distillation of the crude residue in vacuo provides the desired methyl indan-2-carboxylate.

Provenance & Evidence