Synthesis
To a methanol (5 mL) solution of 1-chloro-2-cyclohexylethane (0.50 mmol, purchased from ChemSampCo, Inc.) was added a water (5 mL) solution of sodium bicarbonate (23 mg, 0.28 mmol) and magnesium sulfate (135 mg, 1.10 mmol). The reaction mixture was stirred vigorously at 0°C for 10 min, followed by the addition of potassium permanganate (260 mg, 1.70 mmol). The mixture was warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the solid residue was removed by filtration through a diatomaceous earth pad and the filter cake was washed with ethyl acetate. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, washed with brine (30 mL) and dried with magnesium sulfate. The organic phases were concentrated and purified by fast column chromatography (eluent: hexane/ethyl acetate, 5:1) to afford the target product methyl 2-cyclohexyl-2-oxoacetate (78 mg, 90% yield). Thin Layer Chromatography (TLC, Expanding Agent: Hexane/Ethyl Acetate, 5:1): Rf = 0.40. Mass Spectrometry (ESI) m/z: 171.49 [M + H]+ (Calculated value: 171.16 [M + H]+).
