3-(N,N,N-trimethylammonio)-1-(3,4,5-trimethoxyphenyl)propan-1-one iodide → 2-Propen-1-one, 1-(3,4,5-trimethoxyphenyl)-

HRID 1110823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110823
[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:9])(C)C>O.C(OCC)(=O)C>[CH3:21][O:20][C:12]1[CH:11]=[C:10]([C:8](=[O:9])[CH:7]=[CH2:6])[CH:15]=[C:14]([O:16][CH3:17])[C:13]=1[O:18][CH3:19]

Komponenten

4

Edukt 1

HCID 104092223-(N,N,N-trimethylammonio)-1-(3,4,5-trimethoxyphenyl)propan-1-one iodide

Produkt 1

HCID 104435242-Propen-1-one, 1-(3,4,5-trimethoxyphenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The above iodide (355.9 g, 0.87 mol) was suspended in a mixture of water (3.56 L) and ethyl acetate (2.54 L) and heated under reflux 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 again heated under reflux for 1 hour and the process was repeated once again. The organic extracts were combined, washed with brine, dried (MgSO4), and evaporated to a yellow oil which was crystallized from hexane-ethyl ether to give 1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one: mp 46°-47° C.; NMR (CDCl3) δ 3.94 (s, 3 OCH3), 5.92 (2 d, J=1.5 & 9.0 Hz, CH=CH2), 6.44 (2 d, J=1.5 & 16 Hz, CH=CH2), 7.18 (2 d, J=9.0 & 16 Hz, CH= CH2), 7.28 (ArH).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureThe mixture was cooled
  4. customthe pale yellow organic layer was removed
  5. additionFresh ethyl acetate (2 L) was added
  6. temperaturethe mixture was again heated
  7. temperatureunder reflux for 1 hour
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated to a yellow oil which
  11. customwas crystallized from hexane-ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3c5d4738beed435598f6c09e959f54b1
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977146

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