Potassium Hydroxide → 4-(Difluoromethyl)benzoic acid

HRID 241444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241444
[F:1][CH:2]([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1.[OH-].[K+]>CO>[F:1][CH:2]([F:13])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 22262108Methyl 4-(difluoromethyl)benzoate

Produkt 1

HCID 207393254-(Difluoromethyl)benzoic acidAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dissolve methyl 4-(difluoromethyl)benzoate (2.855 g, 15.336 mmol) in MeOH (30 mL). Add potassium hydroxide (8.41 mL 2 equivalents, 30.7 mmol), and stir the mixture for 16 hours. Concentrate the reaction mixture under reduced pressure, and add EtOAc (100 mL) and 1 N HCl (50 mL). Stir for 30 minutes. Separate the layers. Dry the organics over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the titled compound as a white solid (2.541 g, 96% yield). 1H NMR (399.83 MHz, d6-DMSO) δ 13.29-13.28 (m, 1H), 8.04 (d, J=7.8 Hz, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.24-6.97 (t, J=55.6, 1H).

Aufarbeitung

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. additionadd EtOAc (100 mL) and 1 N HCl (50 mL)
  3. customSeparate the layers
  4. dry with materialDry the organics over Na2SO4
  5. filtrationfilter
  6. customcollect the filtrate
  7. concentrationand concentrate the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6d72ec838ff4ff1be997c257bbd8761
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648200B2

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