Ethyl (E)-4,4,5,5,5-pentafluoropent-2-enoate → (2E)-4,4,5,5,5-Pentafluoro-2-pentenoic acid

Ethyl (E)-4,4,5,5,5-pentafluoropent-2-enoate (5.5 g, 25.2 mmol) was suspended in 10% NaOH (14.5 ml) and heated at reflux until a homogenous solution was obtained (40 min). After cooling to room temperature the mixture was washed with diethylether (2×) and acidified under ice-cooling with concentrated sulfuric acid. The mixture was extracted with diethylether (3×), the combined organic phases were washed with water, dried over magnesium sulfate and the solvent removed under reduced pressure. 2.64 g (13.9 mmol, 55%) were obtained. MS (ES) M/z=189.0 [M−H]−.

1. temperatureheated
2. temperatureat reflux until a homogenous solution
3. customwas obtained (40 min)
4. washwas washed with diethylether (2×)
5. temperaturecooling with concentrated sulfuric acid
6. extractionThe mixture was extracted with diethylether (3×)
7. washthe combined organic phases were washed with water
8. dry with materialdried over magnesium sulfate
9. customthe solvent removed under reduced pressure
10. custom2.64 g (13.9 mmol, 55%) were obtained

ORD record

ord-ba820d34e8444907859ef00547ff1896

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877934B2