Methyl chloroformate → 1,1-Cyclohexanedicarboxylic acid, 4-methyl-, 1,1-dimethyl ester

Participants

Reaction Steps

A solution of methyl 4-methylcyclohexane carboxylic acid (6.5 g, 41.6 mmol) in THF (15 mL) was added dropwise to a solution of lithium diisopropylamine (6.75 g, 62.4 mmol) in THF (60 mL) at −78° C. After stirring for 1 h at the same temperature, a solution of methylchloroformate (5.9 g, 62.4 mmol) in THF (15 mL) was added slowly and the mixture was allowed to warm to room temperature. After 18 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL). THF was removed in vacuo and the aqueous residue was extracted with dichloromethane (100 mL×3). The combined organic layers were dried (MgSO4). After removal of the solvent under reduced pressure, purification by flash column chromatography using an eluting system of hexane/EtOAc (95:5) yielded the title compound as a clear colorless liquid (4.79 g, 54%). MH+215.

Provenance & Evidence