Ethyl 3-phenylprop-2-enoate → 3-Cyano-3-phenylpropanoic acid

HRID 428339

Reaktionsgleichung

Reaktionsgleichung von HRID 428339
[C:1]([O:11]CC)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C-:14]#[N:15].[K+].[Cl-].[NH4+]>CN(C=O)C>[C:14]([CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][C:1]([OH:11])=[O:10])#[N:15]

Komponenten

5

Edukt 3

HCID 7649Ethyl 3-phenylprop-2-enoateHCID 9032Potassium CyanideHCID 25517Ammonium Chloride

Produkt 1

HCID 111946253-Cyano-3-phenylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

Ethyl cinnamate (85.3 g, 0.484 mol), potassium cyanide (64.2 g, 0.986 mol) and ammonium chloride (38.9 g, 0.726 mol) were mixed with aqueous DMF (90%, 360 mL). The mixture was stirred at 105° C. for 7 hours. The somewhat cooled mixture was filtered and most of the DMF was evaporated. The residue was taken up in diethyl ether and 1 M HCl. The aqueous phase was extracted twice with diethyl ether. The combined diethyl ether phases were evaporated and the black oil was suspended in EtOH (200 mL) and 2 M NaOH (250 mL) and stirred at ambient temperature for 2 hours. The mixture was diluted with brine (200 mL) and water (400 mL) and washed twice with diethyl ether. After acidification (12 M HCl) the aqueous phase was extracted three times with diethyl ether. The pooled organic phases were dried (Na2SO4) and the solvent evaporated affording the title compound as a black oil, 74 g (87%): 1H NMR (CDCl3) δ1.05 (d, 3H), 1.17 (d, 3H), 1.22 (d, 6H), 2.68 (dd, 1H), 3.16 (dd, 1H), 3.4 (br, 1H), 3.76 (m, 1H) 4.19 (dd, 1H), 7.31 (m, 5H), 8.9 (br, 1H).

Aufarbeitung

  1. filtrationThe somewhat cooled mixture was filtered and most of the DMF
  2. customwas evaporated
  3. extractionThe aqueous phase was extracted twice with diethyl ether
  4. customThe combined diethyl ether phases were evaporated
  5. stirring2 M NaOH (250 mL) and stirred at ambient temperature for 2 hours
  6. additionThe mixture was diluted with brine (200 mL) and water (400 mL)
  7. washwashed twice with diethyl ether
  8. extractionAfter acidification (12 M HCl) the aqueous phase was extracted three times with diethyl ether
  9. dry with materialThe pooled organic phases were dried (Na2SO4)
  10. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c4c8675097d5431abc0cfdd33feb52bf
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313132B1

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