Thionyl Chloride → 3,4,5-Trihydroxybenzonitrile

HRID 1731780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1731780
[C:1]([NH2:12])(=O)[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.S(Cl)(Cl)=O>C(OCC)(=O)C>[C:1](#[N:12])[C:2]1[CH:3]=[C:4]([OH:5])[C:6]([OH:7])=[C:8]([OH:9])[CH:10]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 692563,4,5-Trihydroxybenzamide

Produkt 1

HCID 137468353,4,5-TrihydroxybenzonitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A reaction mixture containing 23.5 g. of gallamide, 180 ml. of ethyl acetate and 35 ml. of thionylchloride was refluxed for about 18 hours. The volatile contents were removed by evaporation in vacuo and the resulting residue dissolved in 215 ml. of water. This aqueous solution was heated to about 90° C. until the evolution of gas had ceased. The aqueous solution was filtered through charcoal and the water removed from the filtrate by evaporation. 18 g. of gallonitrile were obtained melting at about 219° C. with decomposition (86% yield). Other nitriles useful as starting materials can be prepared similarly.

Aufarbeitung

  1. additionA reaction mixture containing 23.5 g
  2. customThe volatile contents were removed by evaporation in vacuo
  3. dissolutionthe resulting residue dissolved in 215 ml
  4. filtrationThe aqueous solution was filtered through charcoal
  5. customthe water removed from the filtrate by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-35d974ef12da44cf8d8830ca5f50aa58
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04623659

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