m-Chloroperbenzoic acid → 2-(2-Phenylethyl)oxirane

HRID 1351851Notes

Reaction equation

HRID 1351851 reaction equation
[CH:1]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[CH:2][CH2:3][CH3:4].C(=O)([O-])[OH:12].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl.O>[CH2:2]([CH:3]1[CH2:4][O:12]1)[CH2:1][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 1230881-Phenyl-1-buteneHCID 516892Sodium Bicarbonate

Product 1

HCID 1359552-(2-Phenylethyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of but-3-butenylbenzene (3 ml) and sodium hydrogen carbonate (2.5 g) in a mixture of dichloromethane (200 ml) and water (60 ml) was added small portions of m-chloroperbenzoic acid (3.5 g) at room temperature, and the mixture was stirred at the same temperature for 4 hours. After separation, the organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=100:3) to give 2-phenethyloxirane (970 mg).

Workup

  1. customAfter separation
  2. washthe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=100:3)

Sources & evidence

ORD record
ord-bb67ebae380943699536426ea432dd75
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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