Hexafluoropropylene → HCID 18364359, compound

HRID 992142Notes

Reaction equation

HRID 992142 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([F:7])=[C:4]([F:6])[F:5].[CH:10]([O:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]1)=[CH2:11].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:5][C:4]([F:6])([O:21][CH2:20][CH:17]1[CH2:18][CH2:19][CH:14]([CH2:13][O:12][CH:10]=[CH2:11])[CH2:15][CH2:16]1)[CH:3]([F:7])[C:2]([F:9])([F:8])[F:1]

Participants

5

Reactant 3

HCID 8302Hexafluoropropylene3×HCID 11430Potassium CarbonateHCID 163934Cyclohexanemethanol, 4-[(ethenyloxy)methyl]-

Product 1

HCID 18364359HCID 18364359, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Hexafluoropropene (264 g, 1.76 mol) was added dropwise to a mechanically stirred mixture of 1,4-cyclohexanedimethanol vinyl ether (300 g, 1.76 mol), acetonitrile (600 mL), and K2CO3 (121 g, 0.88 mol), at 0° C. under N2. The reaction flask was placed in an ice bath to moderate the exothermic reaction during the addition of hexafluoropropene. After complete addition of hexafluoropropene, the reaction mixture was stirred for an additional hour at room temperature and filtered. The filtrate was added to 1.5 L water and mixed well. The lower layer formed was separated, washed with water (3×300 mL), and concentrated under reduced pressure (approximately 0.05 mm Hg) to afford 1,1,2,3,3,3-hexafluoro-1-{[4 (vinyloxymethyl)cyclo-hexyl]methoxy} propane(cis/trans mixture) as a colorless liquid (428 g, 76% yield); b.p. 55-60° C./0.05 mm Hg; Refractive Index 1.4145 at 23.7° C.; GC/MS: m/z at 320 for M+; 19F and 1H NMR spectral data are consistent with the structure.

Workup

  1. customThe reaction flask was placed in an ice bath
  2. customthe exothermic reaction
  3. filtrationfiltered
  4. additionThe filtrate was added to 1.5 L water
  5. additionmixed well
  6. customThe lower layer formed
  7. customwas separated
  8. washwashed with water (3×300 mL)
  9. concentrationconcentrated under reduced pressure (approximately 0.05 mm Hg)

Sources & evidence

ORD record
ord-5e60696e9bcd4aa7b13807c3fed75cf8
Source dataset
uspto-grants-2002_10
Patent number
US06466730B2

Reaction notes

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