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

HRID 2299637Notes

Reaction equation

HRID 2299637 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-41bdc0fc1cbb47f19629a012c18deb48
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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