m-Chloroperbenzoic acid → 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

HRID 1759535Notes

Reaction equation

HRID 1759535 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:20])[O:19][CH2:18][CH:17]=[CH:16][CH2:15][O:14]1>C(Cl)Cl>[CH3:12][C:13]1([CH3:20])[O:19][CH2:18][CH:17]2[CH:16]([O:9]2)[CH2:15][O:14]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3927074,7-Dihydro-2,2-dimethyl-1,3-dioxepin

Product 1

HCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octaneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of m-chloroperbenzoic acid (74% pure; 78.15 g; 0.33 mole) in methylene chloride (600 ml), was added a solution of 2,2-dimethyl-4,7-dihydro-1,3-dioxepin (II) (41.0 g, 0.32 mole) in methylene chloride (200 ml) during 30 min at room temperature. The mixture was refluxed for 8 hrs and then cooled in ice for 1 hr. The precipitated solid was filtered off and the organic filtrate was washed with 10% aqueous sodium sulfite (2×100 ml), saturated aqueous sodium bicarbonate (3×500 ml), 5% aqueous sodium hydroxide (2×250 ml) and brine (2×200 ml) and dried (MgSO4). Removal of the solvent followed by vacuum distillation of the residual oil gave the epoxide product (III) as a colorless liquid. 36.94 g (80% yield). b.p. 90°-92°/11 mm.

Workup

  1. temperatureThe mixture was refluxed for 8 hrs
  2. temperaturecooled in ice for 1 hr
  3. filtrationThe precipitated solid was filtered off
  4. washthe organic filtrate was washed with 10% aqueous sodium sulfite (2×100 ml), saturated aqueous sodium bicarbonate (3×500 ml), 5% aqueous sodium hydroxide (2×250 ml) and brine (2×200 ml)
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent
  7. distillationfollowed by vacuum distillation of the residual oil

Sources & evidence

ORD record
ord-06af1d6c4365421f85629dd22fd518c3
Source dataset
uspto-grants-1982_07
Patent number
US04341756

Reaction notes

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