反応 #54589

反応方程式

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

Jones reagent

→

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

収率 83.0%

溶媒

acetone

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   その他quenched by the addition of several ml of isopropyl alcohol
3. 3
   その他were removed by evaporation in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in water
5. 5
   抽出extracted several times with ether
6. 6
   洗浄The combined ether extracts were washed with brine
7. 7
   乾燥dried (MgSO4)
8. 8
   その他evaporated in vacuo

実験手順

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.

出典