Acetic Acid → 2-(4-(Hydroxyimino)cyclohexa-2,5-dien-1-ylidene)-2-phenylacetonitrile

HRID 612347

Reaktionsgleichung

[OH-].[K+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O-:14])=O.C(O)(=O)C>CO.O>[OH:14][N:12]=[C:15]1[CH:20]=[CH:19][C:18](=[C:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:10]#[N:11])[CH:17]=[CH:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

60 g of KOH are dissolved in 300 ml of methanol and heated up to 55° C. To the solution are added 32.2 g (0.27 mol) of phenylacetonitrile followed by 30.8 g (0.25 mol) of nitrobenzene. The reaction mixture is stirred at 55° C. for 4 hrs. After cooling, 400 ml of water are added with stirring. The resulting solution is acidified by addition of 110 ml of acetic acid in 100 ml of water, leading to a yellow-orange precipitate. The mixture is then filtered, and the yellow solid is washed with a mixture of methanol and water. The crude product is dried in air, boiled with 150 ml of benzene for 15 min., cooled, filtered and dried under vacuum. 42.6 g (77%) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are obtained in the form of a yellow solid having a melting point of 159-163° C. (dec.).

Aufarbeitung

temperatureAfter cooling
stirringwith stirring
filtrationThe mixture is then filtered
washthe yellow solid is washed with a mixture of methanol and water
dry with materialThe crude product is dried in air
waitboiled with 150 ml of benzene for 15 min.
temperaturecooled
filtrationfiltered
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-fb35ee7f28804bd1807b9f0d9e77c306
Quelldatensatz: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06004724

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