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

HRID 19771

Reaktionsgleichung

Reaktionsgleichung von HRID 19771
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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)−.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0130db70885d4824aae1fb9cc2481a2d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745477B2

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