[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH:8]([CH3:10])[CH3:9].O.[OH-].[Na+]>C(OCC)C>[CH2:7]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:17][CH:18]=1)[CH:8]([CH3:10])[CH3:9]Lithium aluminum hydride (586 mg, 15.4 mmol) was slurried in diethyl ether (50 mL) and cooled in an ice bath. A solution of 4-isobutylbenzaldehyde (5.00 g, 30.9 mmol) in diethyl ether (30 mL) was added dropwise over 10 min and the mixture was stirred for 30 min before successive addition of water (0.6 mL), 15% aq NaOH (0.6 mL), and water (1.8 mL). The resulting precipitate was removed via filtration and the filtrate was dried (MgSO4), filtered, and evaporated in vacuo to give 4-isobutylbenzyl alcohol (4.78 g, 94%). 1H NMR (CDCl3) 7.28 (d, 2H), 7.13 (d, 2H), 4.63 (s, 2H), 2.45 (d, 2H), 1.85 (m, 1H), 0.90 (d, 6H).
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