Sodium Hydroxide → (E)-4,4,5,5-tetrafluoropent-2-enoic acid

HRID 333977Notes

Reaction equation

HRID 333977 reaction equation
[F:1][C:2]([F:13])([CH:10]([F:12])[F:11])/[CH:3]=[CH:4]/[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>C(O)C.O>[F:1][C:2]([F:13])([CH:10]([F:11])[F:12])/[CH:3]=[CH:4]/[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86691166Ethyl (E)-4,4,5,5-tetrafluoropent-2-enoate

Product 1

HCID 86691165(E)-4,4,5,5-tetrafluoropent-2-enoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl (E)-4,4,5,5-tetrafluoropent-2-enoate (15.9 g, 0.08 mol) was dissolved in ethanol (30 ml), 4M NaOH was added (15 ml) and the mixture was stirred at room temperature overnight. The mixture was diluted with water, washed with ethylacetate, acidified with 1M HCl and extracted with ethyl acetate. The organic extract was dried over magnesium sulfate, the solvent was removed under reduced pressure. 12.8 g of a colourless oil were obtained (0.074 mmol, 93%). MS (ESI) m/z=170.9 [M−1]−.

Workup

  1. washwashed with ethylacetate
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-38df27479b75412a8427a10870eababf
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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