4,4,5,5,5-Pentafluoropentan-1-ol → 4,4,5,5,5-Pentafluoropentanoic acid

HRID 1792407Notes

Reaction equation

HRID 1792407 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[F:14][C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[CH2:16][CH2:17][CH2:18][OH:19]>CC(C)=O>[F:14][C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[CH2:16][CH2:17][C:18]([OH:3])=[O:19]

Participants

4

Reactant 2

HCID 5479674,4,5,5,5-Pentafluoropentan-1-olHCID 131709961Jones' reagent

Product 1

HCID 234231634,4,5,5,5-Pentafluoropentanoic acidYield 82.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of Jones reagent (20 ml, 160 mmol) in acetone (20 ml), cooled in an ice bath, a solution of 4,4,5,5,5-pentafluoro-1-pentanol (7.12 g, 40 mmol) in acetone (30 ml) was added dropwise. After remaining ice bath, the mixture was stirred continuously at room temperature for 1 h. The mixture was poured into ice/water and extracted with diethyl ether. Crude ether washed was extracted with aqueous 2 N sodium hydroxide. On the inorganic layer was acidified with aqueous 6 N hydrochloric acid and the organic layer was extracted with diethyl ether. The final extract was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude 4,4,5,5,5-pentafluoropentanoic acid as colorless liquid (6.31 g, 82%), which was used in the next step without further purification.

Workup

  1. extractionextracted with diethyl ether
  2. washCrude ether washed
  3. extractionwas extracted with aqueous 2 N sodium hydroxide
  4. extractionthe organic layer was extracted with diethyl ether
  5. extractionThe final extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7467f471bd84b2393713aa13d35d7c3
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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