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

HRID 596768Notes

Reaction equation

HRID 596768 reaction equation
[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

Participants

7

Reactant 4

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Sources & evidence

ORD record
ord-003e2bfb769e43eeaefbdb815ce032c9
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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