Hydrochloric Acid → 4-Hydroxy-3-methylbenzonitrile

HRID 1003357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003357
Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[CH:6][CH:7]=1.[Cu](C#N)[C:11]#[N:12].O.Cl>CN1C(=O)CCC1.C(OCC)(=O)C>[C:11]([C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[CH:6][CH:7]=1)#[N:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 168964-Bromo-2-methylphenolHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 109645604-Hydroxy-3-methylbenzonitrileAusbeute 133,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixed solution of 10.89 g (58 mmol) of 4-bromo-cresol and 10.39 g (116 mmol) of copper cyanide in 50 ml of NMP was stirred at 190° C. for 2 hours, followed by the addition of 43 g of FeCl3.6H2O, 65 ml of water and 11 ml of concentrated hydrochloric acid. The resulting mixture was stirred at 80° C. for 30 minutes and was then allowed to cool down. Water and ethyl acetate were added to the reaction mixture, followed by separation into a water layer and an organic layer. The organic layer was dried over Na2SO4, and the solvent was then distilled off under reduced pressure. The residue as purified by column chromatography (chloroform/methanol=40/1), whereby 10.32 g of 4-cyanocresol were obtained as a dark brown oil.

Aufarbeitung

  1. temperatureto cool down
  2. customfollowed by separation into a water layer
  3. dry with materialThe organic layer was dried over Na2SO4
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customThe residue as purified by column chromatography (chloroform/methanol=40/1)

Quellen und Nachweise

ORD-Eintrag
ord-38fb365d5a8b4d06abfc58fff0c22699
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046212

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