Acetic Acid → Ethyl 4,4-diethoxy-3-oxobutanoate

HRID 1758901Notes

Reaction equation

HRID 1758901 reaction equation
[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O:7]CC)=O)[CH3:2].[Na].C(O)(=O)C.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19]>>[CH2:11]([O:10][CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:7])[CH2:19][C:18]([O:21][CH2:22][CH3:23])=[O:20])[CH3:12]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 80169Ethyl diethoxyacetateHCID 5360545Sodium

Product 1

HCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoateYield 44.8%

Procedure

To a solution of ethyl diethoxyacetate (24.5 g) in ethyl acetate (12.5 g), metallic sodium (4.2 g) was added, and the resultant mixture was refluxed for about 1.5 hours. The reaction mixture was made acidic with 50% acetic acid and extracted with ether. After removal of the ether from the extract by distillation, the residue was subjected to fractional distillation to give ethyl diethoxyacetoacetate (13.6 g) as a colorless, transparent oil boiling at 84° C./4 mmHg.

Workup

  1. extractionextracted with ether
  2. customAfter removal of the ether from the
  3. extractionextract by distillation
  4. distillationthe residue was subjected to fractional distillation

Sources & evidence

ORD record
ord-80d34e1a886c4efa93249e70cc828f79
Source dataset
uspto-grants-1982_07
Patent number
US04338248

Reaction notes

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