Acetaldehyde → 3-(4-Chlorophenyl)prop-2-enenitrile

HRID 596768

Reaktionsgleichung

Reaktionsgleichung von HRID 596768
[NH2:1]O.[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][CH:10]=[O:11])=[CH:6][CH:5]=1.ClC1C=CC(C=O)=CC=1.CC=O>CCO>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:1])=[CH:6][CH:5]=1.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][CH:10]=[O:11])=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 177AcetaldehydeHCID 787HydroxylamineHCID 77264-ChlorobenzaldehydeHCID 3794977p-Chlorocinnamaldehyde

Produkt 2

HCID 342433-(4-Chlorophenyl)prop-2-enenitrileHCID 3794977p-Chlorocinnamaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Hydroxylamine hydrochloride (13.0 g.) was dissolved in dry methanol (100 ml.) and neutralised to phenolphthalein with a solution of sodium (6 g.) in methanol (60 ml.). The precipitated sodium chloride was filtered off and the filtrate was refluxed with p-chlorocinnamonitrile (9.4 g.) for 2 hrs. Thin layer chromatography showed the reaction to be complete after this time. The reaction mixture was evaporated to dryness in vacuo and the residue was crystallised from ethanol to produce colourless of crystals of p-chlorocinnamamidoxime, 4.16 g. (37%) m.p. 102°-4° λmax (EtOH), 273 nm., ε17500, τ(CDCl3) 2.68 (aromatic), 3.00 (OH), 5.16 (NH2), 3.13 (doublet, J=16 c./sec.), 3.58 (doublet, J=16 c./sec.). p-Chlorocinnamonitrile was prepared by NH2OH treatment and dehydrations of p-chlorocinnamaldehyde (J. Chem. Soc., 1965, 1564). p-Chlorocinnamaldehyde was prepared from p-chloro benzaldehyde and CH3CHO cf. G. Cigarella, E. Occelli, and E. Testa, (J. Med. Chem., 1965, 8, 326).

Quellen und Nachweise

ORD-Eintrag
ord-003e2bfb769e43eeaefbdb815ce032c9
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012377

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