Diethyl Oxalate → Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoate

HRID 37480Notes

Reaction equation

HRID 37480 reaction equation
[Na].[CH3:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([CH2:2][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 74764'-MethoxyacetophenoneHCID 5360545Sodium

Product 1

HCID 287267Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 100 ml of ethanol was dissolved 4.2 g (1.1 eq.) of sodium, and a mixture of 25.0 g of 4-methoxyacetophenone and 27 ml (1.2 eq.) of diethyl oxalate was added dropwise under reflux. After 2 hours' reflux, the resulting crystals were collected by filtration. After 200 ml of 1N hydrochloric acid was added, the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried. The solvent was distilled off. The resulting crystals were collected by filtration with hexane.

Workup

  1. additionwas added dropwise
  2. temperatureunder reflux
  3. temperatureAfter 2 hours' reflux
  4. filtrationthe resulting crystals were collected by filtration
  5. additionAfter 200 ml of 1N hydrochloric acid was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride and dried
  9. distillationThe solvent was distilled off
  10. filtrationThe resulting crystals were collected by filtration with hexane

Sources & evidence

ORD record
ord-3015a4a6254c44be9b79031f810d85b0
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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