Reaktion #54589

Reaktionsgleichung

7-(6-hydroxycyclohex-2-enyl)-hept-5Z-enoic acid

Jones reagent

→

7-(6-oxocyclohex-2-enyl)hept-5Z-enoic acid

Ausbeute 83.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Sonstigequenched by the addition of several ml of isopropyl alcohol
3. 3
   Sonstigewere removed by evaporation in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in water
5. 5
   Extraktionextracted several times with ether
6. 6
   WaschenThe combined ether extracts were washed with brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Sonstigeevaporated in vacuo

Vorschrift

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.

Quelle