[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][OH:9])([CH3:3])[CH3:2]To m-isopropoxybenzaldehyde (38 g, 0.23 mol) in 500 mL of ethanol was added slowly sodium borohydride (12.2 g, 0.32 mol) over a period of 1 h and the mixture was stirred for 2 h, filtered, and concentrated to 100 mL of its volume. The above mixture was diluted with 50 mL of water, neutralized with sulfuric acid solution with cooling, and was extracted with ether (4×100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 36.32 g (95%) of m-isopropoxybenzyl alcohol.
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