Sulfuric Acid → Ethyl 2,4-dioxooctanoate

HRID 1656028Notes

Reaction equation

HRID 1656028 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([O-:4])=O.[CH3:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14].[O-]CC.[Na+].OS(O)(=O)=O>C(O)C.O>[O:4]=[C:2]([CH2:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])[C:1]([O:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 115832-HexanoneHCID 2723922Sodium ethoxideHCID 21943339Ethanedioic acid, monoethyl ester

Product 1

HCID 10998024Ethyl 2,4-dioxooctanoateYield 80.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl oxalate (97.21 g) and hexan-2-one (66.58 g) was added dropwise to a solution of sodium ethoxide (50.1 g) in ethanol (160 ml) at reflux. The resultant mixture was heated at reflux for 2 h. The cooled reaction mixture was poured into a stirring mixture of ice (500 g) and water (100 ml) and the resultant slurry adjusted to pH 1.5(conc.H2SO4). The two layers were separated and the bottom layer extracted with toluene (2×200 ml). The combined organics were washed with brine (200 ml), dried and concentrated in vacuo to give a residue (107 g) which was purified by distillation to afford the title compound as a colourless liquid (67.2 g).

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 2 h
  3. customThe cooled reaction mixture
  4. customThe two layers were separated
  5. extractionthe bottom layer extracted with toluene (2×200 ml)
  6. washThe combined organics were washed with brine (200 ml)
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-530407f4f3a24014934f7642abbc81ff
Source dataset
uspto-grants-1993_10
Patent number
US05252593

Reaction notes

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