Methyl 4-Formylbenzoate → HCID 28738322, compound

Participants

Reaction Steps

To a solution of 4-formyl benzoic acid methyl (10.0 g) in chloroform (300 ml), 4-chlorobenzylamine (11.2 g) was added, and the mixed solution was stirred for 15 min. Then, to the resulting solution, sodium triacetoxyborohydride (16.8 g) was added, and the mixed solution was stirred at room temperature for two hours. To the resulting solution, acetic acid (10.5 ml) was added, and the solution was stirred for four hours. Saturated sodium bicarbonate water was added, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure to remove the solvent, and the resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=15 to 50%) to give methyl 4-{[(4-chlorobenzyl)amino]methyl}benzoate (13.8 g).

Provenance & Evidence