Phenylacetonitrile → 3,4-Dioxo-2,5-diphenylhexanedinitrile

HRID 1287529

Reaktionsgleichung

Reaktionsgleichung von HRID 1287529
[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4](=[O:10])[C:5]([O:7]CC)=O)#[N:2].[C:17]1([CH2:23][C:24]#[N:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]CC.[Na+].[Na]>C(O)(=O)C.O>[C:17]1([CH:23]([C:5](=[O:7])[C:4](=[O:10])[CH:3]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:1]#[N:2])[C:24]#[N:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 8794PhenylacetonitrileHCID 22845Ethyl 3-cyano-3-phenylpyruvateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 252993,4-Dioxo-2,5-diphenylhexanedinitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 3-cyano-3-phenylpyruvate (50.0 g., 0.23 mol.) and 41.0 g. (0.35 mol.) of phenylacetonitrile were added to an alcoholic solution of sodium ethoxide [prepared from 13.4 g. (0.58 g.-atom) of sodium and 360 ml. of absolute ethanol] and the resulting yellow solution was refluxed for 1.75 hours. The cooled solution was diluted with 700 ml. of water and acidified by slow addition of acetic acid. After further cooling in ice, the suspension was filtered and the solid was washed with water and dried to give 2,5-diphenyl-3,4-dioxoadiponitrile, m.p. 284°-286° dec.

Aufarbeitung

  1. temperaturethe resulting yellow solution was refluxed for 1.75 hours
  2. additionThe cooled solution was diluted with 700 ml
  3. temperatureAfter further cooling in ice
  4. filtrationthe suspension was filtered
  5. washthe solid was washed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fc87dec1d50c4f6dae342e7b690a297e
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03984559

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