Hexafluoropropylene → HCID 131729307, compound

HRID 656717Notes

Reaction equation

HRID 656717 reaction equation
FCC(F)(F)C(F)(F)O.[C:10]([CH:17]([O:19][CH2:20][C:21]([C:24]([F:27])([F:26])[F:25])([F:23])[F:22])[OH:18])([C:13]([F:16])([F:15])[F:14])([F:12])[F:11].C(=O)([O-])[O-].[K+].[K+].[F:34][C:35]([F:42])([F:41])[C:36]([F:40])=[C:37]([F:39])[F:38].C(C(COC(C(C(F)(F)F)F)(F)F)(F)F)(F)(F)F>O.C(#N)C>[C:10]([CH:17]([O:18][C:37]([CH:36]([C:35]([F:42])([F:41])[F:34])[F:40])([F:39])[F:38])[O:19][CH2:20][C:21]([C:24]([F:25])([F:26])[F:27])([F:22])[F:23])([C:13]([F:16])([F:15])[F:14])([F:12])[F:11]

Participants

8

Reactant 5

HCID 8302HexafluoropropyleneHCID 11430Potassium CarbonateHCID 16878528302-70-72×HCID 27785191H,1H,2'H-Perfluorodipropyl etherHCID 713784112,2,3,3,3-Pentafluoro-1-(2,2,3,3,3-pentafluoropropoxy)propan-1-ol

Product 1

HCID 131729307HCID 131729307, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

The entire contents of the pentafluoropropanol solution (containing the desired C2F5CH(OH)OCH2C2F5) were placed in a 600 mL Parr reaction vessel along with acetonitrile (167 g) and powdered potassium carbonate (2.9 g). The reactor was sealed, evacuated and heated to 40° C. Hexafluoropropene (64.8 g, 0.43 mole) was added in portions over about two hours and the reactor then held at temperature overnight. The reaction mixture was worked up by pouring into water and washing the resulting lower phase three times with water followed by distillation. The distillation afford a main fraction of boiling point 142° C. The product identity was confirmed by GC-MS and H-1 and F-19 NMR as a mixture of diastereomers in a ratio of 55/45%. One diastereomeric fraction was thought to contain SS and RR enantiomers and the other SR and RS enantiomers. The NMR data showed that the product contained about 4.2% olefin [—OCF═CFCF3] as a 43/57% cis/trans mixture. The excess pentafluoropropanol was converted to CF3CF2CH2OCF2CFHCF3 which was removed during the distillation.

Workup

  1. customThe reactor was sealed
  2. customevacuated
  3. customthen held at temperature overnight
  4. washwashing the resulting lower phase three times with water
  5. distillationfollowed by distillation
  6. distillationThe distillation
  7. customafford a main fraction of boiling point 142° C
  8. customwas removed during the distillation

Sources & evidence

ORD record
ord-c6270098ba2b4cc7bed52f03596adf3c
Source dataset
uspto-grants-2011_12
Patent number
US08071816B2

Reaction notes

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