[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19](O)=[O:20].Cl>C1COCC1.O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][OH:20]Under N2 gas atmosphere, to a stirred mixture of lithium aluminum hydride (0.703 g) in THF (9 mL) was added 2-(3-methoxybenzyl)cyclohexanecarboxylic acid (2.3 g) in THF (9 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for an hour, at ambient temperature for an hour, at 60° C. for 4 hours. The reaction mixture was cooled to 0° C. and was added mixed solution (1M HCl aqueous solution:THF=10:90) dropwise. The resulting mixture was diluted with water and was extracted with diethylether two times. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The mixture was purified by thin-layer chromatography (n-hexane:EtOAc=5:1) to give [2-(3-methoxybenzyl)cyclohexyl]methanol (1.74 g) as a pale yellow oil.
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