Phenylacetonitrile → Ethyl 3-cyano-3-phenylpyruvate

HRID 267754

Reaktionsgleichung

Reaktionsgleichung von HRID 267754
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:15][CH2:16][CH3:17])(=[O:14])[C:11]([O-])=[O:12].[O-]CC.[Na+]>C(O)C>[C:8]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11](=[O:12])[C:10]([O:15][CH2:16][CH3:17])=[O:14])#[N:9]

Komponenten

5

Edukt 3

HCID 8794PhenylacetonitrileHCID 2723922Sodium ethoxideHCID 21943339Ethanedioic acid, monoethyl ester

Produkt 1

HCID 22845Ethyl 3-cyano-3-phenylpyruvate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 117.1 g. (1.0m.) of phenylacetonitrile and 326 ml. (2.4m.) of ethyl oxalate is added to an ethanol solution of sodium ethoxide (prepared by dissolving 23.8 g., 1.08m. of sodium in 500 ml. of absolute ethanol) and refluxed two hours. After cooling, diluting with 2500 ml. of water and extracting with ether, the solution is acidified with acetic acid. The solid is removed and washed with water to give ethyl 3-cyano-3-phenylpyruvate, m.p. 127°-129° C.

Aufarbeitung

  1. additionA mixture of 117.1 g
  2. temperaturerefluxed two hours
  3. temperatureAfter cooling
  4. additiondiluting with 2500 ml
  5. extractionof water and extracting with ether
  6. customThe solid is removed
  7. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-5a583588cf9a4ecd87ac26e99fc1ed56
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03944571

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