Water → 5,5,6,6,6-Pentafluorohexanoic acid

HRID 1267736Notes

Reaction equation

HRID 1267736 reaction equation
S(=O)(=O)(O)[OH:2].[F:6][C:7]([F:18])([C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:9][CH2:10][CH2:11]C#N.[OH2:19]>>[F:6][C:7]([F:18])([C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:9][CH2:10][C:11]([OH:2])=[O:19]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 185462625,5,6,6,6-Pentafluorohexanecarbonitrile

Product 1

HCID 120170595,5,6,6,6-Pentafluorohexanoic acidYield 85%

Procedure

Concentrated sulfuric acid (350 ml) was slowly added dropwise to 5,5,6,6,6-pentafluorohexanecarbonitrile (108 g, 577.20 mmol) at 0° C., and the resulting mixture was stirred for 3 hours at room temperature. Water (350 ml) was slowly added dropwise to this mixture at 0° C., followed by heating under reflux for 12 hours. After cooling to room temperature, water was added to the reaction mixture, which was then extracted three times with dichloromethane. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off to give 5,5,6,6,6-pentafluorohexanoic acid (95.8 g, Yield 85%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling to room temperature
  4. extractionwas then extracted three times with dichloromethane
  5. washThe combined organic layers were washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-016e3135ea034b8c9aac70eef6b191a5
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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