Ethanol → Ethyl 5-acetyl-4-oxohexanoate

Participants

Reaction Steps

Sodium metal (1.5 g) was placed in a 3 L 3-neck round bottom flask equipped with a thermometer, a reflux condenser, and mechanical stirring, and placed in an oil bath. Absolute ethanol (1 L) was added with stirring. When the sodium had dissolved, 350 g of pentan-2,4-dione was added all at once, and then 310 g of ethyl acrylate was added over 30 min. The mixture was refluxed for 2.5 hrs and then allowed to cool to room temperature overnight. Glacial acetic acid (3 mL) was added and the solvent removed by rotary evaporation. The residue was filtered through a pad of diatomaceous earth and distilled through a wiped film still at 0.1 mm. The distillate was redistilled through a 10 inch vacuum jacketed Vigreux column to give 518 g of ethyl 5-acetyl-4-oxohexanoate, BP 84-92° C. at 0.2-0.7 mm.

Provenance & Evidence