Water → 4-(1,1,2,2,2-Pentafluoroethyl)benzoic acid

HRID 19771

Reaction equation

HRID 19771 reaction equation
[F:1][C:2]([F:15])([C:7]1[CH:14]=[CH:13][C:10]([C:11]#N)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].[OH-:16].[K+].[OH2:18]>C(O)C>[F:1][C:2]([F:15])([C:7]1[CH:14]=[CH:13][C:10]([C:11]([OH:18])=[O:16])=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 147741854-(Pentafluoroethyl)benzonitrile

Product 1

HCID 230678834-(1,1,2,2,2-Pentafluoroethyl)benzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-pentafluoroethyl-benzonitrile (2.98 g, 13.5 mmol) and potassium hydroxide (3.03 g, 54.0 mmol) in water (40 mL) and ethanol (20 mL) was heated at reflux for 16 h. After cooling, the solution was partitioned between 1 M aq. hydrochloric acid solution and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced the title compound (2.76 g, 85%). White solid, MS (ISP) 238.9 (M−H)−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureAfter cooling
  4. customthe solution was partitioned between 1 M aq. hydrochloric acid solution and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-0130db70885d4824aae1fb9cc2481a2d
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Linked notes

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