Ammonium Chloride → (5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

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Reaction Steps

A solution of 5-tert-butyl-2-methoxy-3-nitrobenzaldehyde (0.500 g, 2.10 mmol) in methanol (10.5 mL) was cooled to 0° C., and sodium borohydride (0.088 g, 2.31 mmol) was added thereto, followed by stirring the mixture for 15 minutes. Saturated aqueous ammonium chloride solution was added to the reaction solution and the mixture was stirred at room temperature for 10 minutes. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=10/90-50/50) to obtain 0.486 g of captioned compound (96% yield).

Provenance & Evidence