Hydrogen Peroxide → 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

HRID 1759536Notes

Reaction equation

HRID 1759536 reaction equation
[CH3:1][C:2]1([CH3:9])[O:8][CH2:7][CH:6]=[CH:5][CH2:4][O:3]1.C(=O)([O-])[O-:11].[Na+].[Na+].C(#N)C.OO>CO.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:9])[O:8][CH2:7][CH:6]2[CH:5]([O:11]2)[CH2:4][O:3]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 3927074,7-Dihydro-2,2-dimethyl-1,3-dioxepin

Product 1

HCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octaneYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 2,2-dimethyl-4,7-dihydro-1,3-dioxepin (151.4 g, 1.18 mole) in methanol (500 ml) was added anhydrous sodium carbonate (85 g), followed by acetonitrile (150 ml). This suspension was treated with aqueous hydrogen peroxide (30%; 315 ml, 2.78 mole) dropwise at such a rate that the temperature was maintained at 40°. After 5 hr. at 40°, the reaction mixture was poured into brine (1.5 l) and the solution was extracted with n-butanol. The organic layer was washed with brine, dried, and, then, freed of the solvent in vacuo. Vacuum distillation of the residue yielded the product (III) as a colorless liquid (114 g) (67% yield).

Workup

  1. temperaturewas maintained at 40°
  2. extractionthe solution was extracted with n-butanol
  3. washThe organic layer was washed with brine
  4. customdried
  5. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-bb9519cd2b4d48268480606eca1c6785
Source dataset
uspto-grants-1982_07
Patent number
US04341756

Reaction notes

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