Ammonium Chloride → (2-Benzyloxy-5-methoxyphenyl)-(4-methoxyphenyl)methanol

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In a nitrogen stream, to a solution of 2-benzyloxy-5-methoxy-benzaldehyde (2.0 g, 8.25 mmol) in THF (50 mL), a solution of 4-methoxyphenylmagnesium bromide in THF (0.5 M, 19.8 mL) was added dropwise under cooling with ice. The mixture solution was stirred at room temperature for one hour, and then a saturated ammonium chloride aqueous solution was added thereto under cooling with ice and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:1)] to obtain the title compound (2.9 g, 100%).

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