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

HRID 1577307Notes

Reaction equation

HRID 1577307 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-0c5c41ab337a48369e135ee4552c2803
Source dataset
uspto-grants-1981_09
Patent number
US04287362

Reaction notes

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