m-Chloroperbenzoic acid → HCID 57052781, compound

HRID 1596460Notes

Reaction equation

HRID 1596460 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([O:15][CH:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)[CH2:17][CH:18]=[CH2:19])(=[O:14])[CH3:13]>C(Cl)Cl>[C:12]([O:15][CH:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)[CH2:17][CH:18]1[CH2:19][O:9]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21701962HCID 21701962, compound

Product 1

HCID 57052781HCID 57052781, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (2.86 g; 70%) was added to a stirred solution of 4-acetoxy-4-(p-cyanophenyl)-1-butene (2.5 g; 11.6 mmol; from step (a) above) in DCM (20 mL), and the reaction mixture was refluxed for 3 h and then cooled. The m-chlorobenzoic acid was removed by filtration and the filtrate was washed with NaHCO3 (aq.), then with water, the phases were separated, dried, concentrated and purified by column chromatography (DCM) to give the sub-title compound in a 50% yield.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. temperaturecooled
  3. customThe m-chlorobenzoic acid was removed by filtration
  4. washthe filtrate was washed with NaHCO3 (aq.)
  5. customwith water, the phases were separated
  6. customdried
  7. concentrationconcentrated
  8. custompurified by column chromatography (DCM)

Sources & evidence

ORD record
ord-7308403f9ddd40b5a2d2fb87883ac866
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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