m-Chloroperbenzoic acid → (4,4-Dimethylpentyl)oxirane

HRID 1904418Notes

Reaction equation

HRID 1904418 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].ClC1C=C(C=CC=1)C(OO)=[O:15]>ClCCl>[CH3:1][C:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][O:15]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 144593876,6-Dimethyl-1-heptene

Product 1

HCID 20039084(4,4-Dimethylpentyl)oxirane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6,6-dimethyl-1-heptene (5.33 g, 0.0423 mol) and m-chloroperoxybenzoic acid (9.5 g of 85%, 0.048 mol) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. The resulting solution was washed and aqueous sodium hydroxide (3×50 ml of 2M) and dried over sodium sulfate. The solvent was distilled off at atmospheric pressure to yield (4,4-dimethylpentyl)oxirane as a residue, having the following structural characteristics:

Workup

  1. washThe resulting solution was washed
  2. dry with materialaqueous sodium hydroxide (3×50 ml of 2M) and dried over sodium sulfate
  3. distillationThe solvent was distilled off at atmospheric pressure

Sources & evidence

ORD record
ord-4f7289165a914e59b2cdc35716645fc5
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

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