Sodium Hydroxide → HCID 14154687, compound

HRID 1608243Notes

Reaction equation

HRID 1608243 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]2([O:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH2:23][CH2:22]2)=[CH2:20])=[CH:15][CH:14]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2([C:21]3([O:24][C:25]4[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=4)[CH2:22][CH2:23]3)[CH2:20][O:9]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 14154689HCID 14154689, compound

Product 1

HCID 14154687HCID 14154687, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 4.3 g=25 mmol of 80% strength m-chloroperbenzoic acid in 100 ml of chloroform was added dropwise at 20° C. with stirring to a solution of 6.1 g=20 mmol of 1-(4-chlorophenyl)-1-[1-(4-chlorophenoxy)-cyclopropan-1-yl]-ethene (compound from Example 12) in 20 ml of chloroform, and the mixture was stirred for 15 hours at 20° C. and 3 hours under reflux. For work-up, the mixture was shaken three times with 50 ml of 2N sodium hydroxide solution and once with 2N sodium bisulfite solution, washed with water and dried over sodium sulfate, and the solution was concentrated in a water-pump vacuum. The residue was dissolved in twice the volume of ether. After seeding using a crystal from Example 2a, 3.2 g of melting point 96°-97° C. crystallized.

Workup

  1. temperatureunder reflux
  2. washonce with 2N sodium bisulfite solution, washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationthe solution was concentrated in a water-pump vacuum
  5. dissolutionThe residue was dissolved in twice the volume of ether
  6. customcrystallized

Sources & evidence

ORD record
ord-4db7169d0a2544729f9417b03c8b043b
Source dataset
uspto-grants-1989_09
Patent number
US04870088

Reaction notes

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