Methanol → Methyl 2-(4-chlorophenyl)-2-hydroxyacetate

Participants

Reaction Steps

To a stirred solution of 4-chloromandelic acid (10.0 g, 53.6 mmol) in methanol was added sulfuric acid (3.1 mL, 58.9 mmol). The reaction mixture was refluxed for 6 hours. The reaction mixture was concentrated, neutralized with sat. sodium carbonate solution, extracted with ether, washed with brine, dried, and concentrated. Purification by silica gel chromatography (40% ethyl acetate in hexanes) yielded 10.0 g of (4-chlorophenyl)hydroxyacetic acid methyl ester.

Provenance & Evidence