[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10](O)=[O:11])[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.Cl>CCOCC>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)[CH2:2][CH3:3]Trans-4-n-propylcyclohexane carboxylic acid (23.8 g, 0.14 mole), was dissolved in 150 ml of dry ether and added dropwise with stirring into a suspension of 11.4 g (0.3 mole) of LiAlH4 in 300 ml of ether. After the addition the mixture was heated for 2 hours at reflux, and then the supernatant LiAlH4 was decomposed with water while being cooled. The reaction mixture was then poured onto 20% hydrochloric acid and stirred until the inorganic salts dissolved. The product of formula (31) was extracted with diethyl ether; the combined organic phases were washed with water, dried with MgSO4 and concentrated.
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