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

HRID 22371Notes

Reaction equation

HRID 22371 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

1H-NMR spectrum (90 MHz) δHMS CDCl3 : 0.80 (d, J=7Hz, 9H), 0.91 (d, J=7Hz, 3H), 1.0~1.75 (m, 14H), 1.75~2.3 (m, 1H), 4.75~5.03 (m, 2H), 5.35~5.87 (m, 1H) ##STR199## 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-cd5ea0a9ced146419129749a2ff8dd77
Source dataset
uspto-grants-1995_06
Patent number
US05428056

Reaction notes

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