Diethyl Oxalate → Ethyl 2,4-dioxononanoate

HRID 1074131Notes

Reaction equation

HRID 1074131 reaction equation
[Na].[CH3:2][C:3](=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10](OCC)(=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[C:3]([CH2:2][C:10](=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 80512-HeptanoneHCID 5360545Sodium

Product 1

HCID 12777406Ethyl 2,4-dioxononanoateYield 101.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.7 g of sodium metal was dissolved in 92 ml of ethanol. A mixture of 20 g of 2-heptanone and 26 g of diethyl oxalate was dropwise added thereto at 0° C. After the removing the ice bath, the reaction mixture was stirred at room temperature for 3 hours. After evaporation of the reaction mixture, 200 ml of water was added to the resulting syrup, and then an aqueous 10% hydrochloric acid was added with ice-cooling, the pH being adjusted to 1. After extraction with benzene (300 ml×3), the organic layer was washed with 100 ml of water, dried with Glauber's salt (Na2SO4). And concentrated to give ethyl hexanoylpyruvate as a liquid (38 g).

Workup

  1. additionwas dropwise added
  2. customat 0° C
  3. customAfter evaporation of the reaction mixture, 200 ml of water
  4. additionwas added to the resulting syrup
  5. additionan aqueous 10% hydrochloric acid was added with ice-
  6. temperaturecooling
  7. extractionAfter extraction with benzene (300 ml×3)
  8. washthe organic layer was washed with 100 ml of water
  9. dry with materialdried with Glauber's salt (Na2SO4)
  10. concentrationAnd concentrated

Sources & evidence

ORD record
ord-101f1185e5e6457b9111c7c284e823cf
Source dataset
uspto-grants-1990_11
Patent number
US04973576

Reaction notes

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