P,P'-ddd → 1-Chloro-2,2-bis(4-chlorophenyl)ethylene

HRID 1586764Notes

Reaction equation

HRID 1586764 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH:9](Cl)[Cl:10])=[CH:4][CH:3]=1.[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[CH:9][Cl:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6294P,P'-dddHCID 14798Sodium Hydroxide

Product 1

HCID 984911-Chloro-2,2-bis(4-chlorophenyl)ethylene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Into a 4-necked 2-liter flask are placed 500 g (1.56 mole) of 2,2-bis(p-chlorophenyl)-1,1-dichloroethane and 500 ml of dimethyl sulfoxide. A solution of 188 ml (2.34 mole) of 50% sodium hydroxide is added dropwise. The reaction mixture exotherms to 63° during the addition. After the addition, the reaction mixture is stirred for one hour and poured into ice-water. It is extracted with ether. The combined ether extracts are washed with water, saturated sodium chloride solution, and dried over sodium sulfate. Solvent is evaporated to give 311 g of a waxy solid. A portion of the crude product is recrystalized from hexane-ether to give a white solid, mp 65°-7°.

Workup

  1. customInto a 4-necked 2-liter flask are placed
  2. additionThe reaction mixture exotherms to 63° during the addition
  3. additionAfter the addition
  4. extractionIt is extracted with ether
  5. washThe combined ether extracts are washed with water, saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customSolvent is evaporated
  8. customto give 311 g of a waxy solid
  9. customA portion of the crude product is recrystalized from hexane-ether
  10. customto give a white solid, mp 65°-7°

Sources & evidence

ORD record
ord-b2dbec6d86af4ecaad4bb024fb94c445
Source dataset
uspto-grants-1993_06
Patent number
US05216007

Reaction notes

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