[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)=O)C.[Cl-].[Al+3].[Cl-].[Cl-]>COCCOCCOC>[OH:5][CH2:6][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1Sodium borohydride (7.6 g) was added to 200 ml of diglyme, and with stirring at room temperature, a solution of 39.3 g of 4-(2-ethoxycarbonylbenzyl)benzaldehyde in 50 ml of diglyme was added dropwise over the course of 25 minutes. Subsequently, a solution of 9.33 g of anhydrous aluminum chloride in 50 ml of diglyme was added dropwise over the course of 15 minutes. The mixture was stirred at room temperature for 2 hours, and then at 45° to 50° C. for 1 hour. The reaction mixture was poured into about 3 liters of ice water, and stirred. The precipitated crystals were collected by filtration, washed with water, dried, and recrystallized from benzene to afford 28.2 g of 4-(2-hydroxymethylbenzyl)benzyl alcohol as colorless needle-like crystals having a melting point of 101.5° to 102° C.
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