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

HRID 1759537Notes

Reaction equation

HRID 1759537 reaction equation
C(=O)([O-])[O-:2].[Na+].[Na+].[CH3:7][C:8]1([CH3:15])[O:14][CH2:13][CH:12]=[CH:11][CH2:10][O:9]1.C(#N)C1C=CC=CC=1.OO>CO>[CH3:7][C:8]1([CH3:15])[O:14][CH2:13][CH:12]2[CH:11]([O:2]2)[CH2:10][O:9]1

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 7505BenzonitrileHCID 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 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of sodium carbonate (37 g, 0.35 mole) in a mixture of the dioxepin (II) (158.7 g, 1.26 mole), benzonitrile (127.9 g, 1.26 mole) and methanol (150 ml), was added 30% aqueous hydrogen peroxide (42.2 g, 1.24 mole) during 30 min at such a rate that the temperature stayed below 80°. The mixture was kept at 80° with an oil bath for 2 hr, by which time 99% of the hydrogen peroxide added had reacted. The mixture was decanted and, then, subjected to fractional distillation first at 60 mm, then at 20 mm and finally at 6 mm. The fraction boiling at 75°-85° at 6 mm was refractionated at 6 mm to obtain the product (III) as a colorless liquid. (125.5 g) (70% yield). b.p. 82°-87°/6 mm.

Workup

  1. customstayed below 80°
  2. additionadded
  3. customhad reacted
  4. customThe mixture was decanted
  5. distillationsubjected to fractional distillation first at 60 mm

Sources & evidence

ORD record
ord-414b071ab07a47dd900bfe6c957172e5
Source dataset
uspto-grants-1982_07
Patent number
US04341756

Reaction notes

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