Acetic Acid → Ethyl 4-ethoxy-3-oxobutyrate

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.

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

ORD record

ord-e2e2d268d53f4d8386b784d2d31e8c07

Source dataset

uspto-grants-1979_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04168304