Diethylamine → Benzoic acid, 4-[(diethylaMino)Methyl]-, Methyl ester

Participants

Reaction Steps

To a solution of methyl 4-formylbenzoate (300 mg) in 1,2-dichloroethane (6 mL) is added diethylamine (113 μL), and thereto is added sodium triacetoxyborohydride (581 mg) and acetic acid (261 μL) under ice-cooling. The mixture is stirred at room temperature for 18 hours. The reaction mixture is diluted with chloroform (5 mL) and thereto is added a saturated sodium hydrogencarbonate solution (10 mL). After stirring, the organic layer is separated and concentrated. The resultant crude product is purified by column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=70:30→40:60) to give methyl 4-(diethylaminomethyl)benzoate (144 mg, yield; 60%) as an oil. MS (APCI) m/z: 222 [M+H]+

Provenance & Evidence