Hydrochloric Acid → 5-Fluoro-2-hydroxybenzonitrile

HRID 542692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542692
[F:1][C:2]1[CH:10]=[C:6]([CH:7]=[N:8]O)[C:5]([OH:11])=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(OC(=O)C)(=O)C.O.C(O)C>[C:7]([C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:11])#[N:8]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1363350925-Fluorosalicylaldoxime

Produkt 1

HCID 129192915-Fluoro-2-hydroxybenzonitrileAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

5-Fluorosalicylaldoxime (20.2 g, 0.13 mol) was dissolved in acetic anhydride (100 ml), followed by refluxing for 5 hours, distilling off acetic anhydride under reduced pressure after completion of the reaction, adding to the remaining oily material, a solution of KOH (20 g) dissolved in water (100 ml) and ethanol (100 ml), heating the mixture at 80° C. for 2 hours, allowing to cool down to room temperature, adding 6N-hydrochloric acid (50 ml) and water (200 ml) to deposit crystals, filtering the crystals, and recrystallizing from methanol (30 ml) to obtain acicular crystals (15.6 g). M.p. 121°~122° C.

Aufarbeitung

  1. temperatureby refluxing for 5 hours
  2. distillationdistilling off acetic anhydride under reduced pressure
  3. customafter completion of the reaction
  4. additionadding to the remaining oily material
  5. filtrationfiltering the crystals
  6. customrecrystallizing from methanol (30 ml)

Quellen und Nachweise

ORD-Eintrag
ord-187e501355324042b6d32f309d786f9c
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659501

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