7-(6-hydroxycyclohex-2-enyl)hept-5Z-enoic acid → HCID 70594795, compound

HRID 1764167Notes

Reaction equation

HRID 1764167 reaction equation
[OH:1][CH:2]1[CH:7]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH2:4][CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[O:1]=[C:2]1[CH:7]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 705963197-(6-hydroxycyclohex-2-enyl)hept-5Z-enoic acidHCID 131709961Jones' reagent

Product 1

HCID 70594795HCID 70594795, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. additionwas added dropwise
  2. customquenched by the addition of several ml of isopropyl alcohol
  3. customwere removed by evaporation in vacuo
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted several times with ether
  6. washThe combined ether extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-0d6eee147b754830a040c5fae47e97ce
Source dataset
uspto-grants-1978_09
Patent number
US04115438

Reaction notes

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