[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([O:18][C:19]1[CH:31]=[CH:30][C:22]([CH:23]=[CH:24][C:25](OCC)=[O:26])=[CH:21][C:20]=1[O:32][CH3:33])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)O>C(OCC)C.O>[CH2:11]([O:18][C:19]1[CH:31]=[CH:30][C:22]([CH:23]=[CH:24][CH2:25][OH:26])=[CH:21][C:20]=1[O:32][CH3:33])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
A solution of aluminum chloride (7.07 g) in diethyl ether (90 ml) was added dropwise, at 0° C., to a suspension of lithium aluminum hydride (7.59 g) in diethyl ether (300 ml). The mixture was stirred for 15 minutes, to which was added dropwise, at 0° C., a solution of ethyl 4-benzyloxy-3-methoxycinnamate (50,0 g) in diethyl ether (250 ml). The mixture was stirred for one hour at room temperature, to which was added water (200 ml), then, was carefully added 5N sulfuric acid (280 ml) at 0° C. The diethyl ether layer was taken. The aqueous layer was extracted with ethyl acetate. Organic layers were combined, washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (3:2, v/v), 3-(4-benzyloxy-3-methoxyphenyl)-2-propen-1-ol (34.2 g, 79%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 81-82° C.
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