Water → C4F9Och2I

HRID 1267500Notes

Reaction equation

HRID 1267500 reaction equation
[C:1]([O:14][CH2:15]Cl)([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[I-:17].[Na+].O>CC(C)=O>[C:1]([O:14][CH2:15][I:17])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 9925852Butane, 1-(chloromethoxy)-1,1,2,2,3,3,4,4,4-nonafluoro-

Product 1

HCID 9951570C4F9Och2I

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

C4F9OCH2Cl (50 g, 0.175 mole, isomer ratio n/i=95:5) was combined with sodium iodide (52.5 g, 0.38 mole) in acetone (200 g) and heated to reflux overnight. Water was added and the acetone distilled from the reaction vessel using a Dean-Stark apparatus. The product was washed with water to remove residual acetone. Glc of the residue (52.6 g) revealed it to be 82.6 wt. % of the desired product C4F9OCH2I, which was further purified by distillation. The distillation fraction boiling at 110-15° C. was found to be 97.8 wt. % of the desired product with a 96/4 normal to iso ratio.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. distillationthe acetone distilled from the reaction vessel
  4. washThe product was washed with water
  5. customto remove residual acetone
  6. distillationwas further purified by distillation

Sources & evidence

ORD record
ord-99f8b924d79a4eb79f458fb2bf8e7695
Source dataset
uspto-grants-2003_04
Patent number
US06552090B1

Reaction notes

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