m-Chloroperbenzoic acid → HCID 53981625, compound

HRID 269989Notes

Reaction equation

HRID 269989 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)[CH:13]=[CH2:14]>ClCCl>[O:6]1[CH2:14][CH:13]1[CH2:12][C:15]1[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 98555034-allyl-benzonitrile

Product 1

HCID 53981625HCID 53981625, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add a solution of 3-chloro-peroxybenzoic acid (5.44 g, 40.92 mmol), in 25 ml of dichloromethane to a solution of 4-allyl-benzonitrile (2.66 g, 18.60 mmol) in 50 ml of dichloromethane. stir at room temperature overnight. Quench with NaHCO3 (15 ml) saturated solution and wash the organic layer three times with NaHCO3 solution and dry over magnesium sulfate. Evaporate in vacuo, and purify by flash chromatography in Hexane-AcOEt (7:1, 1% Et3N) affording 1.44 g (49%) of the title compound. MS m/z 160 (M+H)+.

Workup

  1. customQuench with NaHCO3 (15 ml) saturated solution
  2. washwash the organic layer three times with NaHCO3 solution
  3. dry with materialdry over magnesium sulfate
  4. customEvaporate in vacuo
  5. custompurify by flash chromatography in Hexane-AcOEt (7:1, 1% Et3N)

Sources & evidence

ORD record
ord-d69f153e72fc40d6a48d50318410d88b
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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