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

HRID 492270Notes

Reaction equation

HRID 492270 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-61bbb6880b5848b48f20d230a18363c6
Source dataset
uspto-grants-2009_05
Patent number
US07531689B2

Reaction notes

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