[C:1]([CH:5]1[CH2:15][CH2:14][CH2:13][CH2:12][C:6]21[O:10][CH:9]([CH3:11])[CH2:8][O:7]2)([CH3:4])([CH3:3])[CH3:2].C(C1CCCCC1=O)(C)(C)C.C(O)C(O)C>[Pd].[Ru].C(O)(C)C>[C:1]([CH:5]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:6]1[O:7][CH2:8][CH:9]([OH:10])[CH3:11])([CH3:4])([CH3:2])[CH3:3]A 500 ml capacity autoclave was charged with 30 g (0.14 mol) of 6-t-butyl-2-methyl-1,4-dioxaspiro[4.5]decane which has been prepared from 2-t-butylcyclohexanone and 1,2-propanediol, 150 ml of isopropyl alcohol, 0.29 g of a catalyst of 5% palladium supported on active carbon and 0.01 gof a catalyst of 5% ruthenium supported on active carbon. The reaction was carried out under a hydrogen pressure of 70 kg/cm2 and at a temperature of 190° C. for 10 hours until completion of the absorption of hydrogen. After the reaction, the catalysts were removed by filtration and the resulting filtrate was subjected to distillation to obtain 24.5 g of 1-(2-t-butylcyclohexyloxy)-2-propanol (b.p.=112° to 113° C./5 mmHg; yield=81%; cis:trans=66:34).
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