Water → Ethyl 4-oxocyclohexanecarboxylate

HRID 1934766Notes

Reaction equation

HRID 1934766 reaction equation
[Cl-].[Li+].N1C=CC=CC=1.O.C([CH:15]1[CH2:20][C:19](C(OCC)=O)([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][CH2:17][C:16]1=[O:31])(OCC)=O>CS(C)=O.C(OCC)(=O)C>[C:21]([CH:19]1[CH2:20][CH2:15][C:16](=[O:31])[CH2:17][CH2:18]1)([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 433294Lithium ChlorideHCID 11758824Triethyl 4-oxocyclohexane-1,1,3-tricarboxylate

Product 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylateYield 46.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 540 ml of dimethyl sulfoxide were added 21.9 g of lithium chloride, 13.9 ml of pyridine and 9.3 ml of water, and the resulting mixture was gently heated under reflux. While refluxing the mixture, 100 ml of a solution of 54.0 g of 2,4,4-tricarbethoxy-cyclohexanone in dimethyl sulfoxide was dropwise added thereto over one hour. After a reaction at the same temperature as above for 2 hours, the mixture was cooled and poured into a mixture of ice water and ethyl acetate, and the organic layer was separated. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by distillation under reduced pressure gave 13.5 g of 4-carbethoxycyclohexanone as a light yellow oily product.

Workup

  1. temperaturethe resulting mixture was gently heated
  2. temperatureunder reflux
  3. additionwas dropwise added
  4. customAfter a reaction at the same temperature as above for 2 hours
  5. temperaturethe mixture was cooled
  6. customthe organic layer was separated
  7. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customPurification of the residue
  11. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-fb60a4da46cd4263bec2333cb5656c2f
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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