Glutaric anhydride → 2'-(4-Carboxybutanoyloxy)-4,4',6'-trimethoxychalcone

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Reaction Steps

Sodium hydride (76 mg of 60% purity) was added with stirring to an ice-cooled solution of 2'-hydroxy-4,4',6'-trimethoxychalcone (500 mg) in 20 ml of tetrahydrofuran. After 10 minutes, a solution of glutaric anhydride (218 mg) in 3 ml of tetrahydrofuran was added. The mixture was stirred at room temperature for 2 hours and evaporated under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate, which was then extracted with 50 ml of 10% aqueous sodium carbonate. The extract was acidified with hydrochloric acid and shaken with 50 ml of chloroform. The chloroform extract was washed with water, dried over Na2SO4 and evaporated under reduced pressure. Crystallization of the residue from benzene gave 75 mg (11% yield) of 2'-(4-carboxybutanoyloxy)-4,4',6'-trimethoxychalcone as pale yellow crystals; m.p. 131°-132° C.

Provenance & Evidence