Water → Ethyl (4Z)-8-oxo-4-octenoate

HRID 1729784Notes

Reaction equation

HRID 1729784 reaction equation
[OH:1][CH:2]1[CH2:9][CH2:8][CH:7]=[CH:6][CH2:5][CH2:4][C:3]1=[O:10].[CH2:11](O)[CH3:12].C1C=CC=CC=1.C([O-])(=[O:22])C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].O>CCOCC>[O:10]=[CH:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][C:2]([O:1][CH2:11][CH3:12])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 2737052-Hydroxy-5-cycloocten-1-oneHCID 21965192Npc112006HCID 178418268HCID 178418268, compound

Product 1

HCID 24972431Ethyl (4Z)-8-oxo-4-octenoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 220 mg. of 2-hydroxy-5-cycloocten-1-one in 5 ml. of 30% ethanol/benzene is added 860 mg. of 85% lead tetraacetate in portions. After about 3 hours at room temperature, water and ether are added to the reaction mixture. The aqueous phase is extracted several times with ether. The combined ether extracts are washed with 2M sodium carbonate and saturated sodium chloride solution, dried over calcium sulfate and evaporated to give ethyl (4Z)-8-oxo-4-octenoate in high purity.

Workup

  1. extractionThe aqueous phase is extracted several times with ether
  2. washThe combined ether extracts are washed with 2M sodium carbonate and saturated sodium chloride solution
  3. dry with materialdried over calcium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-f61c5352f25946a28d95230fc3da0343
Source dataset
uspto-grants-1976_11
Patent number
US03989729

Reaction notes

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