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

HRID 1248747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248747
[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-51ec1de1199247a28bbbdefc3a56315e
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04525577

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