Acetonitrile → 2-Methoxybenzoylacetonitrile

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Reaktionsgleichung

CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].[NH2-].[Na+].[C:15](#[N:17])[CH3:16]>>[CH3:11][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([CH2:16][C:15]#[N:17])=[O:12]

Komponenten

Edukt 3

HCID 6342Acetonitrile

HCID 24533Sodium amide

HCID 61151Methyl 2-Methoxybenzoate

Produkt 1

HCID 49627502-MethoxybenzoylacetonitrileAusbeute 84 %

Versuchsvorschrift

In agreement with this data the condensation of 2-methoxybenzoic acid methyl ester with acetonitrile using sodamide/liquid ammonia gives 2-methoxybenzoylacetonitrile in 84% yield, in contrast this same reaction using sodium hydride in benzene only leads to a 27.4% reaction yield. (Kawase, Bull, Chem. Soc. Japan, Vol. 35 (1962), pages 1869-1871.)

Quellen und Nachweise

ORD-Eintrag: ord-5b875bdeebb3472cbd0b841bc53a3f2e
Quelldatensatz: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04716237

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