Ethanol → Diethyl (3-oxopropyl)malonate

Participants

Reaction Steps

First, 100 ml acrolein was added to a solution of 180 g diethyl bromomalonate, 14 g tributylamine, and 600 ml ethanol while cooling in an ice bath. After 2-3 hours, an additional 1.5 g tributylamine and 20 ml acrolein was added. The stirring was continued for an additional 1 to 2 hours without additional cooling. The reaction mixture was neutralized with 7 ml glacial acetic acid and the ethanol and unreacted acrolein were removed on a rotary evaporator. The residue was diluted with 500 ml benzene and washed with 3× 100 ml H2O and 2× 100 ml saturated NaCl solution. The benzene solution was dired over CaSO4 and rotary evaporated to yield 207 g of yellow oil which was indicated to be 48% product by glc.

Provenance & Evidence