Allyl methacrylate → 2-(7-Methoxynaphthalen-1-yl)acetonitrile

HRID 1454018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454018
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[CH2:13][C:14]#[N:15])=[CH:5][CH:4]=1.C(OCC=C)(=O)C(C)=C>C1(C)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]#[N:15])=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 7274Allyl methacrylateHCID 11287102(7-Methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile

Produkt 1

HCID 112640682-(7-Methoxynaphthalen-1-yl)acetonitrileAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

There are introduced into a 670 litre reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthalenyl)-acetonitrile dissolved in toluene are added as well as 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is followed by vapour phase chromatography. When all the starting substrate has disappeared, the reaction mixture is cooled to ambient temperature and then filtered. After removal of the toluene by evaporation, the resulting solid residue is recrystallised from an ethanol/water (80/20) mixture to give the title product in a yield of 91% and with a chemical purity exceeding 99%.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux
  3. temperatureat reflux
  4. filtrationfiltered
  5. customAfter removal of the toluene
  6. customby evaporation
  7. customthe resulting solid residue is recrystallised from an ethanol/water (80/20) mixture

Quellen und Nachweise

ORD-Eintrag
ord-fe41f5d85626468487389ad3af8e345b
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476751B2

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