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

HRID 2244324

Reaction equation

HRID 2244324 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-ba0ebee87df542b5a70dc5d9a658819f
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Linked notes

Loading…