[C:1]([C:4]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)(O)=[O:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:2][CH2:1][C:4]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]1
A solution of 3.84 g. (0.0123 mole) of 4-carboxy-4-(1-naphthyl)cyclohexanone, ethylene ketal (prepared in Example 29) in 80 ml. of tetrahydrofuran is added to 0.5 g. (0.013 mole) of lithium aluminum hydride in 10 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux the mixture is cooled in ice and treated successively with 0.5 ml. of water, 0.5 ml. of 15% sodium hydroxide solution and 1.5 ml. of water. The resulting inorganic gel is collected on a filter and rinsed with ether. The combined filtrates are evaporated to dryness to give 3.95 g. (99% yield) of 4-hydroxymethyl-4-(1-naphthyl)cyclohexanone, ethylene ketal as an amorphous gum.
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