Ammonium Chloride → [4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methanol

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Reaction Steps

4′-(2-Ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde (2.39 g, 9.70 mmol) was dissolved in a mixed solvent of 1,2-dimethoxyethane (20 mL) and tetrahydrofuran (20 mL). After cooling, sodium borohydride (0.227 g, 6.00 mmol) was added, and the mixture was stirred at the same temperature for 3 hr. Aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-50:50) to give the title compound (3.55 g, yield 98%) as colorless crystals.

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