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

HRID 333075Notes

Reaction equation

HRID 333075 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 was obtained (0.074 mmol, 93%). MS (ESI, negative detection) 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-b422a7f990374c1fa345477bc2e1050c
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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