Citric Acid → 2-Benzoylamino-4-methoxy-3-methylbenzoic acid methyl ester

Participants

Reaction Steps

To an ice cold solution of the above ester (81) (1.5 g, 7.68 mmol) and TEA (2 ml) in dry DCM (30 ml) was added benzoyl chloride (1.4 g, 10 mmol) and the mixture was stirred for four hours at room temperature. Benzoyl chloride (0.14 g, 1 mmol) was added and the mixture was stirred for one hour more at room temperature. A 5% aqueous solution of citric acid was added and the mixture was extracted three times with ethyl acetate. The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried with sodium sulfate and evaporated under reduced pressure. The product was purified by column chromatography on silica gel with eluted with hexane-ethyl acetate which gave the title compound (1.6 g).

Provenance & Evidence