[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([O:18][CH2:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OC(=O)C)C>C1COCC1>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:13][CH2:14][CH:15]([O:18][CH2:19][CH:20]([OH:23])[CH2:21][CH3:22])[CH2:16][CH2:17]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]While keeping inside of a reaction system at a temperature of lower than 10° C., a solution of 5.24 g (16.3 mmol) of 4-(4-pentylcyclohexyl)-(2-oxobutyloxy)cyclohexane produced in Example 3 and dissolved in 35 ml of THF was added dropwise to a mixture of 0.46 g (12.2 mmol) of LAH and 2.5 ml of THF and further stirred for 5 hours at a room temperature. To this solution, under cooling, were added 5 ml of ethylacetate and then 10 ml of 2N aqueous solution of sodium hydroxide to terminate the reaction. After undissolved products were separated, the solvent was distilled off under a reduced pressure and the residue thus obtained was recrystallized from 15 ml of hexane to obtain 5.0 g (yield 95%) of 4-(4-pentylcyclohexyl)-(2-hydroxybutyloxy)cyclohexane.
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