Benzene, (3-chloro-1-propenyl)- → HCID 131719747, compound

HRID 1080883Notes

Reaction equation

HRID 1080883 reaction equation
Cl[CH2:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]1([O-:22])[C:16]([Cl:17])=[C:15]([Cl:18])[C:14]([Cl:19])=[C:13]([Cl:20])[C:12]=1[Cl:21].[Na+].O.C(O)C>C(O)C>[Cl:17][C:16]1[C:15]([Cl:18])=[C:14]([Cl:19])[C:13]([Cl:20])=[C:12]([Cl:21])[C:11]=1[O:22][CH2:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 94242Benzene, (3-chloro-1-propenyl)-HCID 19096565Water ethanolHCID 23663539Sodium pentachlorophenate2×

Product 1

HCID 131719747HCID 131719747, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 500 ml four necked flask equipped with a stirrer, a thermometer and a nitrogen gas inlet, chloromethylstyrene (m/p=60/40) (25 g, 0.161 mole) was dissolved in ethanol (50 ml) at room temperature. A solution of sodium pentachlorophenate (hereinafter abbreviated as Na-PCP) (49 g. 0.170 mole) in a mixed solvent of water/ethanol (1/1, 250 ml) was gradually added dropwise thereto and, after completion of addition, the mixture was reacted at 50° C. for 1 hour. The mixture was cooled and the resulting precipitate was filtered off. The filtrate was concentrated with a rotary evaporator. Then, n-hexane (250 ml) and distilled water (100 ml) were added to the concentrated solution and the mixture was shaken. The aqueous layer was removed and additional distilled water (100 ml) was added. This procedure was repeated to remove unreacted Na-PCP. The hexane layer was evaporated with a rotary evaporator. Then, the solid residue was recrystallized from acetone to obtain (2, 3, 4, 5, 6-pentachlorophenyloxy)methylstyrene of the formula [Ia] as white needle crystals, m.p. 113°-115° C., yield 85%.

Workup

  1. additionwas gradually added dropwise
  2. additionafter completion of addition
  3. customthe mixture was reacted at 50° C. for 1 hour
  4. temperatureThe mixture was cooled
  5. filtrationthe resulting precipitate was filtered off
  6. concentrationThe filtrate was concentrated with a rotary evaporator
  7. distillationThen, n-hexane (250 ml) and distilled water (100 ml)
  8. additionwere added to the concentrated solution
  9. customThe aqueous layer was removed
  10. distillationadditional distilled water (100 ml)
  11. additionwas added
  12. customto remove unreacted Na-PCP
  13. customThe hexane layer was evaporated with a rotary evaporator
  14. customThen, the solid residue was recrystallized from acetone

Sources & evidence

ORD record
ord-808150fffd56471c82e18637aee95a96
Source dataset
uspto-grants-1996_12
Patent number
US05583230

Reaction notes

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