Water → N-methyl-N-(2-carboxybenzyl)-4-carboxymethylaniline

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Reaction Steps

The oily ester (20 g) so obtained was added to a solution of sodium hydroxide (25 g) in a mixed liquor of water (300 ml) and ethanol (100 ml). The mixture was heated under reflux for 2 hours. After most of ethanol was distilled off, the mixture was washed with ether. The aqueous layer was acidified by addition of acetic acid to the layer cooled with ice, and then extracted with ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was recrystallized from methanol-benzene to obtain N-methyl-N-(2-carboxybenzyl)-4-carboxymethylaniline (12.2 g) as colorless prismatic crystals.

Provenance & Evidence