O1CCCC1.C[O:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O.CO>[CH2:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][OH:7])=[CH:14][CH:13]=1)[CH2:16][CH3:17]
Dried tetrahydrofuran (50 ml) in which 10.4 g (58.4 mmol) of 4-n-propylbenzoic acid methyl ester synthesized in step (i) was dissolved was dropwise added to 50 ml of dried tetrahydrofuran containing suspension of lithium aluminium hydride (1.54 g: 40.5 mmol) at a temperature of not more than 10° C. with cooling with ice, and reaction was carried out at a room temperature overnight. After the completion of the reaction, an excess amount of lithium aluminium hydride was reacted with methanol with cooling with ice. Next water and an aqueous solution of hydrochloric acid were successively added to the reaction mixture, and the resultant was extracted with hexane. After the hexane phase was washed with water, hexane was removed from the hexane phase to give 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol.
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