Water → 5,5,6,6,6-Pentafluorohexanoic acid
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
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%).