m-Chloroperbenzoic acid → 1,2-Epoxy-3,7,11-trimethyldodecane

HRID 1974895Notes

Reaction equation

HRID 1974895 reaction equation
[CH3:1][CH:2]([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:3]=[CH2:4].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[O:24]1[CH:3]([CH:2]([CH3:1])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:4]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5284433,7,11-TRIMETHYL-1-DODECENE

Product 1

HCID 139331731,2-Epoxy-3,7,11-trimethyldodecaneYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9.6 g of 3,7,11-trimethyl-1-dodecene in 200 ml of methylene chloride was added 10.8 g of meta-chloroperbenzoic acid at room temperature, and the mixture was stirred at the same temperature for 6 hours. Thereafter, the reaction mixture was filtered and the filtrate was washed successively with aqueous sodium thiosulfate, aqueous sodium hydrogen carbonate and aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was distilled under reduced pressure to give 6.8 g (yield 59%) of 1,2-epoxy-3,7,11-trimethyldodecane. The physical constants of the compound are as follows.

Workup

  1. filtrationThereafter, the reaction mixture was filtered
  2. washthe filtrate was washed successively with aqueous sodium thiosulfate, aqueous sodium hydrogen carbonate and aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-bdaa715a87e74acfb6aec8e0a321f9b4
Source dataset
uspto-grants-1994_02
Patent number
US05284850

Reaction notes

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