m-Chloroperbenzoic acid → 2,2-Diphenyl-3-methyloxirane

HRID 974201Notes

Reaction equation

HRID 974201 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl>[C:1]1([C:7]2([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:8]([CH3:9])[O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 2382071,1-Diphenyl-1-propene

Product 1

HCID 110958912,2-Diphenyl-3-methyloxiraneYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.00 g (10.3 mmol) 1,1-diphenylpropene and 2.09 g (10.4 mmol) 85% m-chloroperbenzoic acid in 15 ml dichloromethane was stirred in the dark at room temperature for 4 hours. The mixture was partitioned between dichloromethane and saturated K2CO3 solution and the organic layer was washed with brine and dried over Na2SO4. This was concentrated to give 2.14 g (98%) of 2,2-diphenyl-3-methyloxirane as a colorless oil.

Workup

  1. customThe mixture was partitioned between dichloromethane and saturated K2CO3 solution
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThis was concentrated

Sources & evidence

ORD record
ord-da846d991cf74451b92885ec26ce4e2e
Source dataset
uspto-grants-1991_11
Patent number
US05068248

Reaction notes

Loading…