Hydrochloric Acid → Ethyl 2,4-dioxooctanoate

HRID 2081282Notes

Reaction equation

HRID 2081282 reaction equation
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[CH3:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17].Cl>C(O)C.O.CCCCCC>[O:5]=[C:3]([CH2:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:2]([O:9][CH2:10][CH3:11])=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 115832-HexanoneHCID 5360545Sodium

Product 1

HCID 10998024Ethyl 2,4-dioxooctanoateYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a solution of sodium (9.3 g) in ethanol (200 ml) was added dropwise a mixture of diethyl oxalate (60 g) and 2-hexanone (40.9 g) with stirring. The reaction mixture was allowed to stand at room temperature for 45 hours. To a mixture of 1N-hydrochloric acid (500 ml) and hexane (500 ml) was added dropwise the reaction mixture with stirring vigorously. After the addition, water (500 ml) was added. The organic layer was washed with water (100 ml ×3), dried, and the solvent was removed by evaporation in vacuo. The residue was distilled under reduced pressure and the distillate at the boiling point of 110° to 111° C. (6 mmHg) was collected to give the desired product (57 g, 70%).

Workup

  1. additionwas added dropwise the reaction mixture
  2. stirringwith stirring vigorously
  3. additionwas added
  4. washThe organic layer was washed with water (100 ml ×3)
  5. customdried
  6. customthe solvent was removed by evaporation in vacuo
  7. distillationThe residue was distilled under reduced pressure
  8. distillationthe distillate at the boiling point of 110° to 111° C. (6 mmHg) was collected

Sources & evidence

ORD record
ord-d099c79ecfae426c80cf62a50effd09f
Source dataset
uspto-grants-1993_02
Patent number
US05183899

Reaction notes

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