m-Chloroperbenzoic acid → 2-(Diphenylmethyl)oxirane

HRID 1897899Notes

Reaction equation

HRID 1897899 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[CH:7]([CH:8]1[CH2:9][O:24]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 153940263,3-Diphenylpropene

Product 1

HCID 125490582-(Diphenylmethyl)oxirane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask was charged with 3,3-diphenylpropene (5.1 g, 26.3 mmol) in 100 ml CH2Cl2. It was followed by portionwise addition of mCPBA (9.1 g, 70% purity, 52.6 mmol) at 0° C. The mixture was stirred at room temperature for 24 h and the reaction was then quenched with 30 ml 1M Na2SO3. The aqueous layer was extracted with CH2Cl2 (2×100 ml). The combined organic phases were washed in turn with saturated NaHCO3, brine, and then dried over anhydrous Na2SO4. Purification by flash chromatography (Hexane/ether=9:1) gave pure 2-benzhydryl-oxirane, 4.7 g (85%).

Workup

  1. customthe reaction was then quenched with 30 ml 1M Na2SO3
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 ml)
  3. washThe combined organic phases were washed in turn with saturated NaHCO3, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customPurification by flash chromatography (Hexane/ether=9:1)

Sources & evidence

ORD record
ord-7cbeed4da9484209aab41472985a90ce
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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