[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=[O:15])([CH3:10])([CH3:9])[CH3:8].O.[OH-].[Na+]>CCOCC>[C:7]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[CH2:14][OH:15])([CH3:10])([CH3:8])[CH3:9]
To a suspension (40 ml) of lithium aluminum hydride (1.38 g, 36.2 mmol) in ether was added dropwise a solution of 3-tert-butylbenzoic acid (3.13 g, 17.6 mmol) in ether (40 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. After completion of the reaction, water (1.38 ml), 15% aqueous sodium hydroxide solution (1.38 ml) and water (4.2 ml) were successively added dropwise slowly under ice-cooling. The obtained solid was filtered with celite, and washed with ethyl acetate. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1, 4:1) to give 3-tert-butylbenzyl alcohol (2.59 g, 90%) as a colorless transparent oil.
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