Dimethyl 1,4-cyclohexanedicarboxylate → 4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

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Reaction Steps

To a stirred solution of dimethyl 1, 4-cyclohexane-dicarboxylate (20 g, Aldrich) in methanol (50 ml) was added a solution of potassium hydroxide (7.3 g) in methanol (75 ml). The reaction mixture was refluxed for 16 hours. After cooling the solvent was removed on a rotary evaporator. The residue was taken up in ether and water and extracted to remove unreacted starting diester. The aqueous layer was acidified with dilute hydrochloric acid and re-extracted with ether. The ether extracts were washed with brine and dried. Evaporation in vacuo gave a solid. Purification was achieved by recrystallization from ethyl acetate to yield 4-methoxycarbonylcyclohexanecarboxylic acid (6.2 g), m.pt 90.9° C.

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