Ethyl Bromide → Diethyl Malonate

Participants

Reaction Conditions

Reaction Steps

In an autoclave, 10.9 g (0.1 mol) of ethyl bromide were added to a solution of 2.96 g (20 mmol) of disodium malonate and 0.64 g (2 mmol) of tetrabutylammonium bromide in 5 ml of water and 10 ml of tert-butyl methyl ether. The mixture was heated to 100° C. over a period of 30 minutes, with the pressure in the autoclave rising to 3.5 bar. After a reaction time of 3½ hours at 100° C., the mixture was cooled to room temperature and depressurized. The aqueous phase was brought from pH 4.2 to pH 5.5 using 1 M sodium hydroxide solution and extracted with tert-butyl methyl ether (2×5 ml). The combined organic phases were dried over sodium sulfate and analyzed by gas chromatography (internal standard: dimethyl succinate). The product yield was 45 percent.

Provenance & Evidence