Acetic Anhydride → 1,1-Cyclohexanediacetic acid mono methyl ester

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Reaction Steps

A solution of 1,1-cyclohexanediacetic acid (5.0 g) in acetic anhydride (8.0 mL) was stirred under reflux for 5 hours. The solution was then concentrated under reduced pressure and distilled with toluene azeotropically. To a solution of the resulting residue in methanol (15.2 mL) was added boron trifluoride diethyl ether complex (1.58 mL) at room temperature. The solution was stirred at room temperature for 2 hours. Saturated aqueous sodium carbonate solution was added to the solution and it was washed with diethyl ether. The aqueous layer was neutralized by addition of conc. hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound (4.21 g).

Provenance & Evidence