solution was concentrated and distilled in a Kugelrohr apparatus (100 °C pot temperature, 30 mm) to provide 0.342 g (50%) of 2-methylcyclohexanol. Analysis by VPC (10% TCEP, 6 ft x l/a in., 110 °C) revealed no observable amounts of the cis isomer. The cis and trans isomers may also be distinguished by the NMR signal of the proton on the carbon adjacent to the oxygen. The cis isomer exhibits a multiple! at 3.7 ppm while the trans isomer exhibits a multiplet at 2.9 ppm. Again, none of the cis isomer could be detected.Acknowledgment is made to the donors of the Petroleum Research Fund, administered by the American Chemical Society, for support of this research.
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