Reaktionsgleichung
[I-].C[N+]([CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=1)=O)(C)C.[C:22]([O:25][CH2:26][CH3:27])(=O)C.[OH2:28]>>[CH3:21][O:20][C:12]1[CH:11]=[C:10]([CH:8]=[CH:7][C:6]([CH:7]=[CH:8][C:10]2[CH:27]=[C:26]([O:25][CH3:22])[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)=[O:28])[CH:15]=[C:14]([O:16][CH3:17])[C:13]=1[O:18][CH3:19]Komponenten
Versuchsvorschrift
3-(N,N,N-trimethylammonio)-1-(3,4,5-trimethoxyphenyl)propan-1-one iodide (355.9 g, 0.87 mole) was suspended in a mixture of water (3.56 L) and of ethyl acetate (2.54 L) and refluxed with rapid stirring for 2-3 hours. The mixture was cooled and the pale yellow organic layer was removed. Fresh ethyl acetate (2 L) was added and the mixture was refluxed for 1 hour, and the process was repeated once again. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, and evaporated to dryness to provide a yellow oil, which was crystallized from hexane/ether to give 3,4,5-trimethoxyphenylvinyl ketone (m.p. 45°-47° C.). 200 MHz 1H NMR (CDCl3): δ 3.94 (9H, s, 3 OCH3), 5.92 (1H, dd, J=1.5 Hz, J=9 Hz), 6.44 (1H, dd, J=1.5 Hz, J=1.5 Hz, J=16 Hz), 7.18 (1H, dd, J=16 Hz, J=9 Hz), 7.28 (2H, H2 and H6).
Aufarbeitung
- temperaturerefluxed
- temperatureThe mixture was cooled
- customthe pale yellow organic layer was removed
- additionFresh ethyl acetate (2 L) was added
- temperaturethe mixture was refluxed for 1 hour
- washwashed with brine
- dry with materialdried over anhydrous MgSO4
- customevaporated to dryness
- customto provide a yellow oil, which
- customwas crystallized from hexane/ether
Quellen und Nachweise
- ORD-Eintrag
- ord-1d344d6e311a4bccb1db48ae8e8a97d1
- Quelldatensatz
- uspto-grants-1991_04
- Patentnummer
- US05010100
Verknüpfte Notizen
Wird geladen…