Acetic Acid → Ethyl 4-ethoxy-3-oxobutyrate

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.

1. customrose to 50° C
2. customthe solvent was evaporated off on a rotary evaporator in vacuo
3. extractionthe mixture was extracted twice with 250 ml of methylene chloride each time
4. dry with materialthe combined organic phases were dried over magnesium sulphate
5. distillationthe residue was distilled

ORD record

ord-a7bf75bf7eae4b00b70d93c2adcf9636

Source dataset

uspto-grants-1978_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04120956