m-Chloroperbenzoic acid → 2-(4-Chlorophenyl)-2-methyloxirane

HRID 2232263Notes

Reaction equation

HRID 2232263 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH3:8])=[CH2:7])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2([CH3:8])[CH2:7][O:19]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 743814-Chloro-alpha-methylstyrene

Product 1

HCID 1605872-(4-Chlorophenyl)-2-methyloxiraneYield 52.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred and cooled solution (0°-5° C.) of 4-chloro-α-methylstyrene (15.2g) in chloroform (350 mL), add m-chloroperbenzoic acid (21.6 g). Stir the reaction mixture for 1 hr by which time all starting material will haye reacted to give virtually a single product. Remove the m-chlorobenzoic acid formed by washing chloroform solution with aqueous NaHCO3 followed by water (150 mL). Dry the chloroform solution (Na2SO4) and evaporate to dryness to provide a colorless oil. Distill the oil in vacuo (1 mm) and collect fractions distilling between 65°-72° to give the title compound (8.8 g).

Workup

  1. stirringStir the reaction mixture for 1 hr by which time all starting material
  2. customwill haye reacted
  3. customto give virtually a single product
  4. customRemove the m-chlorobenzoic acid
  5. customformed
  6. washby washing chloroform solution with aqueous NaHCO3
  7. dry with materialDry the chloroform solution (Na2SO4)
  8. customevaporate to dryness
  9. customto provide a colorless oil
  10. distillationDistill the oil in vacuo (1 mm)
  11. customcollect fractions
  12. distillationdistilling between 65°-72°

Sources & evidence

ORD record
ord-710d854744154d3ab61259f48f5ea990
Source dataset
uspto-grants-1988_11
Patent number
US04788190

Reaction notes

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