Toluene → Methyl 4-(pyridin-2-YL)benzoate

HRID 1277005

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.C#C.[C:15]1(C)[CH:20]=CC=[CH:17][CH:16]=1>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Co+2]>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:20][N:11]=2)=[CH:6][CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

24.0 g (150 mmol) of 4-cyanobenzoic acid methyl ester (Fluka, Buchs, Switzerland) in 150 ml of toluene are placed under an acetylene atmosphere in an autoclave and 0.30 g (1.6 mmol) of cobaltocene (=dicyclopentadienylcobalt; Aldrich, Milwaukee, USA) is added. The mixture is then subjected to an acetylene pressure of 15 atm, heated at 1 80° C. and stirred for 12 hours. After cooling and release of the pressure, 9.5 g of active carbon are added to the black suspension; the mixture is diluted with 250 ml of toluene, stirred for 30 min, filtered and concentrated by evaporation. Crystallisation from warm ether by the addition of hexane yields the title compound: m.p. 96° C.; TLC (hexane/ethyl acetate 4:1): Rf =0.37; FAB MS (M+H)+ =214. Further product can be obtained from the mother liquor by column chromatography (SiO2, hexane/ethyl acetate 19:1-4:1).

Aufarbeitung

additionis added
temperatureAfter cooling
additionrelease of the pressure, 9.5 g of active carbon are added to the black suspension
stirringstirred for 30 min
filtrationfiltered
concentrationconcentrated by evaporation
customCrystallisation
temperaturefrom warm ether
additionby the addition of hexane

Quellen und Nachweise

ORD-Eintrag: ord-82c33becb60740b5a2cf6fd5af567601
Quelldatensatz: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06166004

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