Benzaldehyde → 3-Benzoylpropionitrile

HRID 597553

Reaktionsgleichung

Reaktionsgleichung von HRID 597553
CN(C)C=O.[CH:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C-]#N.[Na+].[C:17](#[N:20])[CH:18]=[CH2:19]>O>[C:6]([CH2:19][CH2:18][C:17]#[N:20])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 6228Dimethylformamide2×HCID 7855AcrylonitrileHCID 8929Sodium Cyanide2×

Produkt 1

HCID 1384653-Benzoylpropionitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

320 ml of absolute dimethylformamide, 42.5 g (0.4 mol) of freshly distilled benzaldehyde and 9.8 g (0.2 mol) of sodium cyanide are introduced into a 500 ml 4-necked flask equipped with dropping funnel, stirrer, KOH drying tube and internal thermometer. A week exothermic reaction takes place after the addition of sodium cyanide to the reaction mixture and the temperature rises from 30° to 34° C. The reaction mixture is stirred for 15 minutes at a reaction temperature of 30° C and a solution of 15.9 g (0.3 mol) of freshly distilled acrylonitrile and 80 ml of absolute dimethylformamide is introduced dropwise into the reaction mixture in the course of one hour at the same temperature. Stirring is then continued for 1/4 hours at the same temperature. The reaction mixture, which is now very creamy, is poured on to 800 ml of water and vigorously shaken. The aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform. The combined chloroform solutions are vigorously washed with water and dried over MgSO4 and the chloroform is distilled off. Inoculating crystals are added to the residue. β-Benzoyl-propionitrile then crystallises at once. It is suction filtered and washed with ethanol. 26.6 g of β-benzoylpropionitrile are obtained. M.p.: 69° C.

Aufarbeitung

  1. customequipped
  2. customA week exothermic reaction
  3. customrises from 30° to 34° C
  4. stirringStirring
  5. waitis then continued for 1/4 hours at the same temperature
  6. stirringvigorously shaken
  7. extractionThe aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform
  8. washThe combined chloroform solutions are vigorously washed with water
  9. dry with materialdried over MgSO4
  10. distillationthe chloroform is distilled off
  11. additionInoculating crystals are added to the residue
  12. customβ-Benzoyl-propionitrile then crystallises at once
  13. filtrationfiltered
  14. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5715a0e797ff4131ab7f9d1ebafbbff2
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014889

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