Diethyl Oxalate → Ethyl 2,4-dioxononanoate

Participants

Reaction Steps

4.7 g of sodium metal was dissolved in 92 ml of ethanol. A mixture of 20 g of 2-heptanone and 26 g of diethyl oxalate was dropwise added thereto at 0° C. After the removing the ice bath, the reaction mixture was stirred at room temperature for 3 hours. After evaporation of the reaction mixture, 200 ml of water was added to the resulting syrup, and then an aqueous 10% hydrochloric acid was added with ice-cooling, the pH being adjusted to 1. After extraction with benzene (300 ml×3), the organic layer was washed with 100 ml of water, dried with Glauber's salt (Na2SO4). And concentrated to give ethyl hexanoylpyruvate as a liquid (38 g).

Provenance & Evidence