Butanal → Butanedioic acid, 2-(1-oxobutyl)-, 1,4-diethyl ester

Participants

Reaction Steps

A mixture of 86 g of diethyl maleate, 144 g of butyraldehyde and 4 g of dibenzoyl peroxide was boiled at reflux for 20 hours. After completion of the reaction, the excess butyraldehyde was firstly distilled off over a Vigreux column and then the yellow coloured crude product was taken up in 250 ml of hexane and washed with 200 ml of 5% (wt./vol.) sodium hydrogen carbonate solution and 200 ml of water. The aqueous phases were back-extracted with a small amount of hexane. The combined organic phases were dried over sodium sulphate and freed from solvent on a rotary evaporator. Distillation of the resulting crude product in a high vacuum over a Vigreux column gave 104.5 g (85.6%) of diethyl 2-butyrylsuccinate as a slightly yellow coloured liquid; b.p. 84°-90° C./0.08 Torr.

Provenance & Evidence