(1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanol → 4-Carboxy-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane

HRID 36833Notes

Reaction equation

HRID 36833 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][O:9][C:6]([CH3:11])([O:7][CH2:8]1)[O:5][CH2:4]2.CC(C)=[O:14].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:2]([C:3]12[CH2:4][O:5][C:6]([CH3:11])([O:7][CH2:8]1)[O:9][CH2:10]2)([OH:14])=[O:1]

Participants

4

Reactant 2

HCID 13547990(1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanolHCID 131709961Jones' reagent

Product 1

HCID 199362494-Carboxy-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  1. customThe excess oxidant is removed by the addition of 2-propanol until a green color
  2. customis obtained
  3. customthe solvents are evaporated under reduced pressure
  4. customThe residue is partitioned between dichloromethane (100 mL) and water (50 mL)
  5. customthe layers are separated
  6. washThe organic layer is washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d4c714964b194172822a3fb5f67121e7
Source dataset
uspto-grants-1995_05
Patent number
US05417959

Reaction notes

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