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

HRID 1708952Notes

Reaction equation

HRID 1708952 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-134c938d6c594e0fabf826984059b922
Source dataset
uspto-grants-1990_08
Patent number
US04946857

Reaction notes

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