Reacción #54589

Ecuación de reacción

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

Jones reagent

→

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

Rendimiento 83.0%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Otroquenched by the addition of several ml of isopropyl alcohol
3. 3
   Otrowere removed by evaporation in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in water
5. 5
   Extracciónextracted several times with ether
6. 6
   LavadoThe combined ether extracts were washed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Otroevaporated in vacuo

Procedimiento

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.

Fuente