Reaction #54589

ord-fdc04057727d4890b409e5dd55d330c6

Reaction equation

O=C(O)CCC/C=C\CC1C=CCCC1O
7-(6-hydroxycyclohex-2-enyl)-hept-5Z-enoic acid
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
→
O=C(O)CCC/C=C\CC1C=CCCC1=O
7-(6-oxocyclohex-2-enyl)hept-5Z-enoic acid
Yield 83.0%

Reactants

O=C(O)CCC/C=C\CC1C=CCCC1O
7-(6-hydroxycyclohex-2-enyl)-hept-5Z-enoic acid
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
—
resultant mixture

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added dropwise
  2. 2
    Otherquenched by the addition of several ml of isopropyl alcohol
  3. 3
    Otherwere removed by evaporation in vacuo
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in water
  5. 5
    Extractionextracted several times with ether
  6. 6
    WashThe combined ether extracts were washed with brine
  7. 7
    Dryingdried (MgSO4)
  8. 8
    Otherevaporated in vacuo

Procedure

A solution of 15.8 g of 7-(6-hydroxycyclohex-2-enyl)-hept-5Z-enoic acid (as obtained by ether-pentane extraction as described above) in 300 ml of acetone was stirred with ice-bath cooling as 30 ml of standard Jones reagent was added dropwise. The resultant mixture was stirred for 10 min at 0° and then quenched by the addition of several ml of isopropyl alcohol. After stirring for another 10 min at 0° the solvents were removed by evaporation in vacuo. The residue was dissolved in water and extracted several times with ether. The combined ether extracts were washed with brine, dried (MgSO4) and evaporated in vacuo to yield 13.0 g of crude 7-(6-oxocyclohex-2-enyl)hept-5Z-enoic acid as a yellow oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04149017uspto-grants-1979_04