Ethyl Acetoacetate → HCID 22902405, compound

Participants

Reaction Steps

32 ml of ethyl acetoacetate were added dropwise with ice cooling to 100 ml of 21% strength sodium ethylate solution in ethanol (=solution I). After 20 minutes 75 ml of a solution of 50 g of 3,4-dimethoxybenzoyl chloride in 150 ml of tetrahydrofuran (=solution II) were added dropwise to the reaction mixture. Subsequently further quanities of solutions I and II were added dropwise to the reaction mixture alternately, each at intervals of 20 minutes, until the reaction mixture contained a total of 190 ml of solution I and 176 ml of solution II. After 16 hours the precipitated salts were filtered out, washed with tetrahydrofuran and then suspended in water. The aqueous mixture was acidified to pH 1 with ice cooling and was extracted with methyl tert-butyl ether. The extract was evaporated to dryness, and 45 g of ethyl 2-acetyl-2-(3,4-dimethoxybenzoyl)-acetoacetate were obtained as a yellow oil.

Provenance & Evidence