Potassium Fluoride → Sevoflurane

HRID 2352079Notes

Reaction equation

HRID 2352079 reaction equation
[F-:1].[K+].[CH:3]([O:12][CH2:13][Cl:14])([C:8]([F:11])([F:10])[F:9])[C:4]([F:7])([F:6])[F:5]>O>[CH:3]([O:12][CH2:13][F:1])([C:8]([F:11])([F:10])[F:9])[C:4]([F:7])([F:6])[F:5].[CH:3]([O:12][CH2:13][Cl:14])([C:4]([F:5])([F:6])[F:7])[C:8]([F:11])([F:10])[F:9]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 101306212-(Chloromethoxy)-1,1,1,3,3,3-hexafluoropropane

Product 2

HCID 5206SevofluraneHCID 101306212-(Chloromethoxy)-1,1,1,3,3,3-hexafluoropropane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
185 °C

Procedure

A 1 liter stainless steel autoclave (Parr) was charged with 127.3 g (2.19 mole) of potassium fluoride and 434.6 g (2.01 mole) of (CF3)2CHOCH2Cl. The autoclave was then sealed and the reaction mass heated at 185° C. for 19 hours, during which time a pressure of 280 psi developed. The reactor was then cooled, the contents treated with water and the organic material distilled to afford 241 g (1.21 mole) of (CF3)2CHOCH2F and 80 g (0.4 mole) of (CF3)2CHOCH2Cl, corresponding to a 60% conversion (75% yield). The structure of (CF3)2CHOCH2F (Sevoflurane), b.p. 56° C., may be confirmed by the following instrumental data:

Workup

  1. customThe autoclave was then sealed
  2. temperatureThe reactor was then cooled
  3. distillationthe organic material distilled

Sources & evidence

ORD record
ord-9b5a493fbbb24fd3917634302d496ccf
Source dataset
uspto-grants-1989_10
Patent number
US04874901

Reaction notes

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