Hexafluoroacetone → CH2=C(CF3)CF2Ocf(CF3)2

HRID 1178834Notes

Reaction equation

HRID 1178834 reaction equation
[CH2:1]=[C:2]([C:7]([O:10]S(F)(=O)=O)([F:9])[F:8])[C:3]([F:6])([F:5])[F:4].[C:15](O[K])([C:21]([F:24])([F:23])[F:22])([C:17]([F:20])([F:19])[F:18])[F:16].[F-].[K+].FC(F)(F)C(C(F)(F)F)=O>O.COCCOCCOC>[CH2:1]=[C:2]([C:7]([O:10][C:15]([C:21]([F:24])([F:23])[F:22])([C:17]([F:20])([F:19])[F:18])[F:16])([F:9])[F:8])[C:3]([F:6])([F:5])[F:4]

Participants

7

Reactant 4

HCID 12695HexafluoroacetoneHCID 522689Potassium FluorideHCID 87741755CH2=C(CF3)CF2Oso2FHCID 178506340HCID 178506340, compound

Product 1

HCID 131726622CH2=C(CF3)CF2Ocf(CF3)2Yield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

CH2═C(CF3)CF2OSO2F (10 g, 0.041 mole) is added at 20° C. to (CF3)2CFOK, prepared from freshly dried potassium fluoride (KF) (2.4 g, 0.041 mole), hexafluoroacetone (HFA) (9.3 g, 0.056 mole) and dry diglyme (10 ml). The reaction mixture is agitated for 2 hours and then poured into water, the organic layer separating. The organic layer is washed with dilute hydrochloric acid, then sodium bicarbonate solution, then water, after which it is dried over magnesium sulfate (MgSO4). Distillation of the reaction mixture gives CH2═C(CF3)CF2OCF(CF3)2 (10.2 g, 75% yield, b.pt. 87–88° C.).

Workup

  1. customthe organic layer separating
  2. washThe organic layer is washed with dilute hydrochloric acid
  3. dry with materialsodium bicarbonate solution, then water, after which it is dried over magnesium sulfate (MgSO4)
  4. distillationDistillation of the reaction mixture

Sources & evidence

ORD record
ord-1a3de0f532f4482eb5a079a83273e2c0
Source dataset
uspto-grants-2007_10
Patent number
US07276624B2

Reaction notes

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