[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H][H].[CH2:14]1[O:17][CH:15]1[CH3:16].Cl>O1CCCC1>[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:11])([CH3:4])([CH3:2])[CH3:3].[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:14][CH:15]([OH:17])[CH3:16])([CH3:4])([CH3:2])[CH3:3]To a 300 ml round bottom flask provided with a Dimroth condenser and a dropping funnel, 7.5 g (0.194 mol) of sodium hydride (62 weight % mineral oil dispersion type) and 30 ml of tetrahydrofuran were added and heated at 60° C. under a nitrogen gas flow. Then, to this solution a mixture of 30.0 g (0.192 mol) of 2-tert-butylcyclohexanol (cis:trans=8:2) and 30 ml of tetrahydrofuran was added dropwise in approximately 30 minutes, and the mixed solution was stirred under reflux for 24 hours until the generation of hydrogen gas had stopped. The reacted mixed solution was cooled to 40° C., and after dropwise adding 11.1 g (0.192 mol) of propyleneoxide to the mixed solution, the solution was further stirred under reflux for 48 hours. The mixed solution was neutralized by 3N hydrochloric acid, and the organic layer was separated from the water layer. Distillation was then conducted and 9.9 g of 2-tert-butylcyclohexanol and 24.2 g of 1-(2-tert-butylcyclohexyloxy)-2-propanol (cis:trans=8:2) (bp. 112° to 113° C./5 mm Hg) were obtained in a 59% yield. Further, the cis-trans isomers of 1-(2-tert-butylcyclohexyloxy)-2-propanol were separated from each other by column chromatography using a developing solvent composed of Kieselgel 60 (trademark) of Merck Corporation and hexane:ethyl acetate =95:5.
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