Ethanol → 2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)(1,1'-biphenyl)-3-methanol

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Reaction Steps

To 2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (50.0 g) was added ethanol (400 mL), and the mixture was stirred for 10 min. To this solution was added dropwise at 25° C. a solution separately prepared by dissolving sodium hydroxide (1.0 g) in water (125 mL) and adding sodium borohydride (3.28 g), and the wall-side of the titration equipment was washed with water (50 mL). The mixture was stirred at 25° C. for 1 hr, activated carbon (10.0 g) was added, and the mixture was stirred for 1 hr. The insoluble material was removed by filtration, and washed with a mixed solution (200 mL) of water.ethanol (1:4). 6M Hydrochloric acid was added to the filtrate at 25° C. to adjust the mixture to pH 3.0. Then, 1 mol/L aqueous sodium hydroxide solution was added to adjust the mixture to pH 7.0. The mixture was concentrated to 200 mL, the attachment on the wall was washed with a mixed solution (50 mL) of water-ethanol (1:4), and the mixture was stirred at 50° C. for 30 min. Water (50 mL) was added dropwise, and the mixture was stirred at 50° C. for 30 min. After stirring at 25° C. for 2 hr, water (450 mL) was added dropwise, and the mixture was stirred at 25° C. for 2 hr. The precipitated solid was collected by filtration, and the solid was washed with water (500 mL) and dried at 60° C. under reduced pressure to give {2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol (47.6 g).

Provenance & Evidence