Water → 2-Methyl-3-(4-formylphenyl)-2-propenonitrile

HRID 67267

Reaktionsgleichung

Reaktionsgleichung von HRID 67267
C[O-].[Na+].[CH:4](=[O:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.C(P([CH:20]([CH3:23])[C:21]#[N:22])(CC)=O)C.O>CO.C(O)(=O)C>[CH3:23][C:20](=[CH:9][C:8]1[CH:11]=[CH:12][C:5]([CH:4]=[O:13])=[CH:6][CH:7]=1)[C:21]#[N:22]

Komponenten

7

Edukt 4

HCID 962WaterHCID 12173TerephthalaldehydeHCID 10942334Sodium MethoxideHCID 159170772-(Diethylphosphoryl)-propionitrile

Produkt 1

HCID 545580302-Methyl-3-(4-formylphenyl)-2-propenonitrileAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

360 g of a 30% solution of sodium methylate in methanol are added dropwise to a suspension of 134 g of terephthalaldehyde in 500 ml of methanol at 20°-25° C. 191 g of 2-(diethylphosphoryl)-propionitrile [prepared by the method of M. L. Raggio and D. S. Watt, J. Org. Chem. 41, 1873 (1976)] are now slowly added dropwise to the resulting reaction solution at 20°-25° C. The reaction mixture is stirred at room temperature for 6 hours and then poured onto 1,000 ml of water, and the aqueous suspension is adjusted to a pH value of 7 with acetic acid. The product which has precipitated is filtered off, dried and then chromatographed on silica gel. 35 g (20.5% of theory) of 2-methyl-3-(4-formylphenyl)-2-propenonitrile of the formula ##STR32## and then obtained in the form of colourless crystals having a melting point of 63°-64° C.

Aufarbeitung

  1. addition41, 1873 (1976)] are now slowly added dropwise to the resulting reaction solution at 20°-25° C
  2. customThe product which has precipitated
  3. filtrationis filtered off
  4. customdried
  5. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2ceca3f7db644803b0100fe27256f864
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346016

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