Aniline → (7-Methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile

HRID 1297555

Reaktionsgleichung

Reaktionsgleichung von HRID 1297555
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=O)=[CH:5][CH:4]=1.[C:14]([CH2:16]C(O)=O)#[N:15].C(O)(=O)CCCCCC.NC1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[CH2:16][C:14]#[N:15])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 6115AnilineHCID 8094Heptanoic AcidHCID 9740Cyanoacetic acidHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 11287102(7-Methoxy-3,4-dihydronaphthalen-1-yl)acetonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

There are introduced into a 670 litre reactor 85.0 kg of 7-methoxy-1-tetralone, 60.3 kg of cyanoacetic acid and 15.6 kg of heptanoic acid in toluene in the presence of 11.0 kg of aniline. The mixture is heated at reflux. When all the starting substrate has disappeared, the solution is cooled and filtered. The precipitate obtained is washed with toluene and then the filtrate obtained is washed with a 2N sodium hydroxide solution and subsequently with water until neutral. After removal of the solvent by evaporation, the resulting solid is recrystallised from an ethanol/water (80/20) mixture to give the title product in a yield of 87% and with a chemical purity exceeding 99%.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. temperaturethe solution is cooled
  4. filtrationfiltered
  5. customThe precipitate obtained
  6. washis washed with toluene
  7. customthe filtrate obtained
  8. washis washed with a 2N sodium hydroxide solution and subsequently with water until neutral
  9. customAfter removal of the solvent
  10. customby evaporation
  11. customthe resulting solid is recrystallised from an ethanol/water (80/20) mixture

Quellen und Nachweise

ORD-Eintrag
ord-9fb7f36916614ee6b46ce33571ffa2bc
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250531B2

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