Acetovanillone → (Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone

HRID 55611

Reaktionsgleichung

Reaktionsgleichung von HRID 55611
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[Cl:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]Cl>C(#N)C>[Cl:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=1[O:11][CH3:12]

Komponenten

5

Edukt 3

HCID 2214AcetovanilloneHCID 11430Potassium CarbonateHCID 64321151,4-Dichloro-cis-2-butene

Produkt 1

HCID 57454977(Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanoneAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-hydroxy-3-methoxyacetophenone (16.6 g, 10 mmole), K2CO3 (14 g, 100 mmol) and cis-1,4-dichloro-2-butene (Aldrich, 15 g, 120 mmol) in acetonitrile (250 ml) was heated at reflux for 2.5 hours. The mixture was filtered and concentrated to an oil, Purification was by flash chromatography. The fractions containing the purest product were combined and concentrated to give white crystals, 7.7 g, 30%. This was recrystallized from ether to give analytical pure (Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone (2.72 g), m.p.=64°-66° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated to an oil, Purification
  5. additionThe fractions containing the purest product
  6. concentrationconcentrated
  7. customto give white crystals, 7.7 g, 30%
  8. customThis was recrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-f07fcc574af340f597a9c1798b025a1a
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624927

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