m-Chloroperbenzoic acid → 4,4-Dimethyl-3,7-dioxa-bicyclo[4.1.0]heptane

HRID 56432Notes

Reaction equation

HRID 56432 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:7][CH:6]=[CH:5][CH2:4][O:3]1.ClC1C=C(C=CC=1)C(OO)=[O:14]>ClCCl>[CH3:1][C:2]1([CH3:8])[CH2:7][CH:6]2[CH:5]([O:14]2)[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 125367332,2-dimethyl-3,6-dihydro-2H-pyran

Product 1

HCID 1180362274,4-Dimethyl-3,7-dioxa-bicyclo[4.1.0]heptaneYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,2-dimethyl-3,6-dihydro-2H-pyran (4.0 g, 36 mmol) in dichloromethane (20 mL) was added 3-chloroperoxybenzoic acid (18.4 g, 107 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was then diluted with dichloromethane, and washed with saturated aqueous sodium sulfite and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (5.0 g, crude) as a yellow oil, which was directly used in the next step without further purification.

Workup

  1. washwashed with saturated aqueous sodium sulfite and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2dd7331ef1cc450ca46ca7997db579d9
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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