反応 #65111

反応方程式

4-(hydroxymethyl)-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane

Jones reagent

→

4-carboxy-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane

溶媒

acetone

反応条件

後処理

1. 1
   その他The excess oxidant is removed by the addition of 2-propanol until a green color
2. 2
   その他is obtained
3. 3
   その他the solvents are evaporated under reduced pressure
4. 4
   その他The residue is partitioned between dichloromethane (100 mL) and water (50 mL)
5. 5
   その他the layers are separated
6. 6
   洗浄The organic layer is washed with water
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   その他evaporated under reduced pressure

実験手順

To a solution of 4-(hydroxymethyl)-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane (10.0 g, 0.062 mol) in 200 mL of acetone is added Jones reagent (chromium trioxide and sulfuric acid) until an orange color persisted. The excess oxidant is removed by the addition of 2-propanol until a green color is obtained and the solvents are evaporated under reduced pressure. The residue is partitioned between dichloromethane (100 mL) and water (50 mL) and the layers are separated. The organic layer is washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 4-carboxy-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane.

出典