Reaktion #65111

Reaktionsgleichung

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

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle