Acetic Acid → Ethyl 4-ethoxy-3-oxobutyrate

Participants

Reaction Steps

2.2 mol of sodium ethylate in ethanol -- prepared from 55.2 g (2.2 mols) of sodium and 500 ml of ethanol -- were diluted with 500 ml of tetrahydrofuran. 164.5 g (1 mol) of γ-chloroacetoacetic acid ethyl ester were added to the solution, at room temperature, sufficiently rapidly that the reaction temperature rose to 50° C. The mixture was then cooled to room temperature, 72 g (1.2 mols) of glacial acetic acid were added, the solvent was evaporated off on a rotary evaporator in vacuo, the residue was shaken with 200 ml of water, the mixture was extracted twice with 250 ml of methylene chloride each time, and the combined organic phases were dried over magnesium sulphate. The solvent was stripped off in vacuo and the residue was distilled. 123.7 g (71% of theory) of γ-ethoxyacetoacetic acid ethyl ester of boiling point 75° C./3 mm Hg were obtained.

Provenance & Evidence