Methyl Acetate → Methyl 4,4-diethoxy-3-oxobutanoate

HRID 66959

Reaction equation

HRID 66959 reaction equation
C(O[C:4](=[O:12])[CH:5]([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])C.[CH3:13][O:14][C:15](=[O:17])[CH3:16].[Na]>>[CH2:10]([O:9][CH:5]([O:6][CH2:7][CH3:8])[C:4](=[O:12])[CH2:16][C:15]([O:14][CH3:13])=[O:17])[CH3:11]

Participants

4

Reactant 3

HCID 6584Methyl Acetate2×HCID 80169Ethyl diethoxyacetateHCID 5360545Sodium3×

Product 1

HCID 15445487Methyl 4,4-diethoxy-3-oxobutanoate

Procedure

Ethyldiethoxyacetate (32 g.) and methylacetate (25 g.) are placed in a flask equipped with stirrer and reflux condenser and heated to reflux. Metallic sodium wire (6.5 g.) is introduced into the flask in small portions and heating continued until the sodium is completely dissolved. Methylacetate (25 g.) and metallic sodium wire (6.5 g.) are then added and heating continued until the solution is clear. The mixture is cooled, a large volume of ice water cautiously added and the mixture extracted with ether. The aqueous solution is acidified with hydrochloric acid at 10° C. to 15° C. and the desired product extracted with ether. The ethereal extract is dried (Na2SO4), the ether removed and the residue distilled in vacuo to give methyl γ,γ-diethoxyacetoacetate.

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. temperatureheated to reflux
  4. temperatureheating
  5. dissolutionis completely dissolved
  6. temperatureheating
  7. temperatureThe mixture is cooled
  8. extractionthe mixture extracted with ether
  9. customis acidified with hydrochloric acid at 10° C. to 15° C.
  10. extractionthe desired product extracted with ether
  11. extractionThe ethereal extract
  12. dry with materialis dried (Na2SO4)
  13. customthe ether removed
  14. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-f26830b71c91465e8f8b89f5b78b81d3
Source dataset
uspto-grants-1982_08
Patent number
US04343942

Linked notes

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