Sulfuric Acid → 2,2,3,4,4,4-Hexafluorobutyric acid

HRID 843368

Reaction equation

HRID 843368 reaction equation
[F:1][C:2]([F:11])([CH:5]([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:13].[K+].[K+].S(=O)(=O)(O)O>O>[F:1][C:2]([F:11])([CH:5]([F:10])[C:6]([F:9])([F:7])[F:8])[C:3]([OH:13])=[O:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24502Potassium DichromateHCID 5339902,2,3,4,4,4-Hexafluorobutan-1-ol

Product 1

HCID 226171612,2,3,4,4,4-Hexafluorobutyric acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

First, 9.1 g (50 mmol) of 2,2,3,4,4,4-hexafluorobutan-1-ol was dissolved in 40 ml of water, to which 14.7 g (50 mmol) of potassium dichromate and 17 ml of concentrated sulfuric acid, and the mixture was heated at 100° C. for 3 hours. After cooling, the reaction mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 9.0 g of 2,2,3,4,4,4-hexafluorobutyric acid.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7dd410fa401a49dba6d450d19267e1cd
Source dataset
uspto-grants-2002_04
Patent number
US06376710B2

Linked notes

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