Acetic Acid → Ethyl 2,6-dicyano-3-methylhex-2-enoate

HRID 1155638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155638
[C:1]([CH2:3][CH2:4][CH2:5][C:6]([CH3:8])=O)#[N:2].[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12](=[O:13])[C:11]([C:9]#[N:10])=[C:6]([CH3:8])[CH2:5][CH2:4][CH2:3][C:1]#[N:2])[CH3:16]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 82611Hexanenitrile, 5-oxo-HCID 517165Ammonium Acetate

Produkt 1

HCID 54500111Ethyl 2,6-dicyano-3-methylhex-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-cyanopropyl ketone (55.5 g, 0.5 mole), ethyl cyanoacetate (56.5 g, 0.5 mole), acetic acid (6.0 g, 0.1 mole), ammonium acetate (3.85 g, 0.05 mole) and toluene (50 ml) was refluxed while azeotropically removing the water of reaction formed. After 10 hours the solution was vacuum distilled and a fraction (b.p. 145° C.-153° C., 0.5 torr) was collected. Total yield was 77.0 g or 74.7 percent. Analysis by infrared spectroscopy confirmed the product's identity as:

Aufarbeitung

  1. temperaturewas refluxed
  2. customwhile azeotropically removing
  3. customthe water of reaction
  4. customformed
  5. distillationvacuum distilled
  6. customa fraction (b.p. 145° C.-153° C., 0.5 torr) was collected

Quellen und Nachweise

ORD-Eintrag
ord-635f760d90f242918e80cc2dd1ec4fa8
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04332734

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