m-Chloroperbenzoic acid → Methyl 2-(4-chlorophenyl)oxirane-2-carboxylate

HRID 1612767Notes

Reaction equation

HRID 1612767 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:22][CH2:13]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11735736Methyl 2-(4-chlorophenyl)acrylate

Product 1

HCID 19776488Methyl 2-(4-chlorophenyl)oxirane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 19.6 g of methyl 2-(4-chlorophenyl)acrylate in 200 ml of dry chloroform, under an inert atmosphere are added 47.06 g of 55% m-chloroperbenzoic acid and the resulting solution is refluxed for 18 hours. The mixture is then cooled and the solid removed by filtration. Evaporation in vacuo of the filtrate and chromatography of the residue on silica-gel affords methyl 2-(4-chlorophenyl)-2,3-epoxy-propionate as a colourless oil.

Workup

  1. temperaturethe resulting solution is refluxed for 18 hours
  2. temperatureThe mixture is then cooled
  3. customthe solid removed by filtration
  4. customEvaporation in vacuo of the filtrate and chromatography of the residue on silica-gel

Sources & evidence

ORD record
ord-fda53885c7374412b65bdb45a195c0f0
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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