m-Chloroperbenzoic acid → HCID 14695112, compound

HRID 486627Notes

Reaction equation

HRID 486627 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2=[CH2:14])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]32[O:26][CH2:14]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 14695111HCID 14695111, compound

Product 1

HCID 14695112HCID 14695112, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(4-Chlorobenzyl)-2,5,5-trimethyl-1-methylenecyclopentane (6.1 g) was dissolved in 60 ml of chloroform, followed by the addition of 8.5 g of m-chloroperbenzoic acid. The resultant mixture was stirred for 5 hours under ice cooling. Calcium hydroxide (4.0 g) was added, followed by stirring at room temperature for 30 minutes. A solid thus precipitated was filtered off. From the chloroform layer as the filtrate, chloroform was distilled off under reduced pressure to obtain a colorless oily substance. The substance was subjected to and purified by chromatography on a silica gel column (eluent: 6:1 mixed solvent of n-hexane and methylene chloride), thereby obtaining 2.0 g of 4-(4-chlorobenzyl)-4,7,7-trimethyl-1-oxaspiro[2.4]heptane used in the above Preparation Example.

Workup

  1. customA solid thus precipitated
  2. filtrationwas filtered off
  3. distillationFrom the chloroform layer as the filtrate, chloroform was distilled off under reduced pressure
  4. customto obtain a colorless oily substance
  5. custompurified by chromatography on a silica gel column (eluent: 6:1 mixed solvent of n-hexane and methylene chloride)

Sources & evidence

ORD record
ord-837d6bba712a4a5ea7a2ea01033808fc
Source dataset
uspto-grants-1994_03
Patent number
US05292764

Reaction notes

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