m-Chloroperbenzoic acid → HCID 14421498, compound

HRID 1722353Notes

Reaction equation

HRID 1722353 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:31])C=1>ClCCl>[CH2:16]([O:15][C:5]1[C:6]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH:2]1[CH2:3][O:31]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 14421497HCID 14421497, compound

Product 1

HCID 14421498HCID 14421498, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g (0.0684 mol) of 1-allyl-2-benzyloxy-3-cyclopentylbenzene are dissolved in 200 ml of dichloromethane. While stirring and cooling in an ice bath, 14 g (0.081 mol) of m-chloroperbenzoic acid are added in portions. The mixture is allowed to reach room temperature and, after 2.5 h, a further 5 g of m-chloroperbenzoic acid are added. The mixture is further stirred at room temperature overnight, and then the precipitated m-chlorobenzoic acid is removed by filtration and the filtrate is concentrated in vacuo. The oily residue is thoroughly stirred with n-pentane and filtered, and the filtrate is washed three times with 2N sodium hydroxide solution and then once with saturated brine. Drying over sodium sulfate is followed by removal of the solvent by distillation in vacuo. 23.9 g of (2-benzyloxy-3-cyclopentylbenzyl)oxirane are obtained as an oil.

Workup

  1. temperaturecooling in an ice bath
  2. stirringThe mixture is further stirred at room temperature overnight
  3. customthe precipitated m-chlorobenzoic acid is removed by filtration
  4. concentrationthe filtrate is concentrated in vacuo
  5. stirringThe oily residue is thoroughly stirred with n-pentane
  6. filtrationfiltered
  7. washthe filtrate is washed three times with 2N sodium hydroxide solution
  8. dry with materialDrying over sodium sulfate
  9. customis followed by removal of the solvent by distillation in vacuo

Sources & evidence

ORD record
ord-9965e7fa671a4271887576d419a2d6ba
Source dataset
uspto-grants-1989_08
Patent number
US04855323

Reaction notes

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