m-Chloroperbenzoic acid → HCID 86735256, compound

HRID 461404Notes

Reaction equation

HRID 461404 reaction equation
[Cl:1][CH:2]=[CH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[Cl:1][CH:2]=[CH:3][CH2:4][C:5]12[O:19][CH:6]1[CH:7]=[CH:8][CH:9]=[CH:10]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 138711(3-Chloroallyl)benzene

Product 1

HCID 86735256HCID 86735256, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

16.6 g of o-chloroallylbenzene was dissolved in 100 ml of chloroform and to the mixture was added dropwise, while maintaining the temperature at 0° - 5° C, 25 g of m-chloroperbenzoic acid dissolved in 600 ml of chloroform. The resulting mixture was allowed to stand at the same temperature for 72 hours. After the separated m-chlorobenzoic acid was filtered off, the filtrate was washed with 10% sodium hydroxide solution, then with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain the residue, which was distilled under reduced pressure to give 7.2 g (yield 38.8%) of o-chloroallylbenzene oxide having a boiling point of 93° C/3 mmHg.

Workup

  1. additionwas added dropwise
  2. temperaturewhile maintaining the temperature at 0° - 5° C
  3. filtrationAfter the separated m-chlorobenzoic acid was filtered off
  4. washthe filtrate was washed with 10% sodium hydroxide solution
  5. dry with materialwith water and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto obtain the residue, which
  8. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-218d6475585744b69942cb07ebfba8ed
Source dataset
uspto-grants-1977_12
Patent number
US04062862

Reaction notes

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