Reacción #65111

Ecuación de reacción

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

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente