Peracetic Acid → HCID 14721902, compound

HRID 257608Notes

Reaction equation

HRID 257608 reaction equation
CC(OO)=[O:3].[Cl:6][C:7]1[CH:24]=[CH:23][C:10]([CH2:11][C:12]2[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[C:13]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:9][CH:8]=1>C(O)(=O)C.ClC(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][C:12]23[O:3][C:13]2([C:19]([O:21][CH3:22])=[O:20])[C:14]([CH3:18])([CH3:17])[CH2:15][CH2:16]3)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 6585Peracetic Acid2×HCID 118327721-(4-Chlorobenzyl)-3,3-dimethyl-2-methoxycarbonylcyclopent-1-ene

Product 1

HCID 14721902HCID 14721902, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

23.5 g (3 equivalents) "PROXITANE 4002" (Trade Mark: 36-40% (w/w) peracetic acid in acetic acid) were added to 9.8 g (35.1 mmols) 1-(4-chlorobenzyl)-3,3-dimethyl-2-methoxycarbonylcyclopent-1-ene prepared as described in Example 1 (f) in 90 ml trichloromethane. The resulting mixture was refluxed for 3 hours and then extracted twice with 50 ml aliquots of trichloromethane, backwashed once with 50 ml dilute aqueous sodium bicarbonate solution and twice with 50 ml aliquots of saturated aqueous sodium metabisulphite solution, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate and flashed to give 12 g of a pale yellow oil which crystallised on cooling. Trituration in 30/40 petroleum gave 5.8 g 1-(4-chlorobenzyl)-1,2-epoxy-3,3-dimethyl-2-methoxy-carbonylcyclopentane as a white crystalline solid, m.pt. 86°-87° C. Yield: 56%.

Workup

  1. customprepared
  2. temperatureThe resulting mixture was refluxed for 3 hours
  3. extractionextracted twice with 50 ml aliquots of trichloromethane
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulphate

Sources & evidence

ORD record
ord-cf89f99c249a4f83a48dc7a3fd1dd247
Source dataset
uspto-grants-1993_11
Patent number
US05262543

Reaction notes

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