Hexafluoroacetone → HCID 13980927, compound

HRID 1614785Notes

Reaction equation

HRID 1614785 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([C:5]([F:8])([F:7])[F:6])=[O:4].[F-:11].[K+].[F:13][C:14](=[CH2:18])[C:15](Cl)=[O:16]>COCCOCCOC>[F:13][C:14](=[CH2:18])[C:15]([O:4][C:3]([F:11])([C:5]([F:8])([F:7])[F:6])[C:2]([F:10])([F:9])[F:1])=[O:16]

Participants

5

Reactant 3

HCID 12695HexafluoroacetoneHCID 522689Potassium Fluoride2×HCID 27833352-Fluoroacryloyl chloride

Product 1

HCID 13980927HCID 13980927, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

15.3 g (0.092 mol) of hexafluoroacetone were passed with stirring in the course of 30 minutes at a temperature of 25° C. into a suspension of 5.34 g (0.092 mol) of dried potassium fluoride in 25 ml of dry diethylene glycol dimethyl ether, and the potassium fluoride dissolved. After a further 2 hours of stirring, unreacted hexafluoroacetone was distilled off under reduced pressure (water jet pump). 10 g (0.092 mol) of α-fluoroacryloyl chloride were added at a temperature of 25° C. with stirring to the remaining solution in the course of 5 minutes, and a colorless solid precipitated. The reaction mixture was stirred at a temperature of 25° C. for a further 80 minutes, and 0.005 g of hydroquinone monomethyl ether were then added, which has followed by distillation under a pressure of 40 mbar. 17.6 g (74 percent of theory) of perfluoroisopropyl α-fluoroacrylate having a boiling point of 40° C. (under 165 mbar) were obtained.

Workup

  1. distillationunreacted hexafluoroacetone was distilled off under reduced pressure (water jet pump)
  2. stirringwith stirring to the remaining solution in the course of 5 minutes
  3. customa colorless solid precipitated
  4. stirringThe reaction mixture was stirred at a temperature of 25° C. for a further 80 minutes
  5. addition0.005 g of hydroquinone monomethyl ether were then added
  6. distillationwhich has followed by distillation under a pressure of 40 mbar

Sources & evidence

ORD record
ord-c14638817d734fd6a885e124a7d88593
Source dataset
uspto-grants-1993_03
Patent number
US05198925

Reaction notes

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