Acetic Acid → Ethyl 4-ethoxy-3-oxobutyrate

Participants

Reaction Steps

2.2 moles of sodium ethylate in ethanol--prepared from 55.2 g (2.2 moles) of sodium in 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 mol) of glacial acetic acid were added, the solvent was evaporated off on a rotary evaporator, the residue was shaken with 250 ml of water and extracted twice with 250 ml of methylene chloride at a time, and the combined organic phases were dried over magnesium sulphate. The solvent was stripped off under reduced pressure and the residue was distilled. 123.6 g (71% of theory) of γ-ethoxyacetoacetic acid ethyl ester of boiling point 75° C./3 mm Hg were thus obtained.

Provenance & Evidence