Water → 2H,2H,3H,3H-Perfluoroheptanoic acid
Reaction equation
[F:1][C:2]([F:18])([C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][CH2:4][CH2:5]C#N.[OH2:19].S(=O)(=O)(O)[OH:21]>>[F:1][C:2]([F:18])([C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][CH2:4][C:5]([OH:21])=[O:19]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
4,4,5,5,6,6,7,7,7-Nonafluoroheptanecarbonitrile (4.7 g, 17.2 mmol) was stirred in concentrated sulfuric acid (15 ml) for 3 hours at room temperature, cooled to 0° C. and mixed with water (15 ml), followed by heating under reflux for 12 hours. The reaction mixture was extracted with dichloromethane and the resulting organic layer was washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was distilled off to give 4,4,5,5,6,6,7,7,7-nonafluoroheptanoic acid (5.1 g, quantitative) as an oil.
Workup
- temperatureby heating
- temperatureunder reflux for 12 hours
- extractionThe reaction mixture was extracted with dichloromethane
- washthe resulting organic layer was washed with water and saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-aa4a13603fb3489abfa3dcd7e6da9df2
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552069B1
Reaction notes
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