Acetone → Ethyl 2,4-dioxovalerate

HRID 1250277Notes

Reaction equation

HRID 1250277 reaction equation
[O-]CC.[Na+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][C:16]([CH3:18])=[O:17].O>C(O)C>[CH3:14][CH2:13][O:12][C:5]([C:6]([CH2:15][C:16]([CH3:18])=[O:17])=[O:8])=[O:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxide

Product 1

HCID 69208Ethyl 2,4-dioxovalerate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 125 ml of ethanol were dissolved 14.2 g of sodium ethoxide, followed by the dropwise addition of a mixed liquid of 25 ml of diethyl oxalate and 13.5 ml of acetone over 20 minutes. The resulting mixture was stirred at room temperature for 3 hours. After the completion of the reaction, water was added to the reaction mixture. Ethanol was then evaporated under reduced pressure. The residue was extracted with chloroform. After the chloroform layer was washed with water, it was dried over anhydrous magnesium sulfate. The solvent was then evaporated, whereby ethyl acetopyruvate (1) was obtained (O. S., Coll. Vol. 1, 238(1958)).

Workup

  1. additionwas added to the reaction mixture
  2. customEthanol was then evaporated under reduced pressure
  3. extractionThe residue was extracted with chloroform
  4. washAfter the chloroform layer was washed with water, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-320c485b8519412d8ce2868af5668b24
Source dataset
uspto-grants-2002_01
Patent number
US06337400B1

Reaction notes

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