Methyl iodide → Michler's ethylene

HRID 579936

Reaktionsgleichung

Reaktionsgleichung von HRID 579936
C[Mg]I.[Mg].[CH3:5]I.[CH3:7][N:8]([CH3:26])[C:9]1[CH:25]=[CH:24][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)=O)=[CH:11][CH:10]=1.[Cl-].[NH4+]>C(OCC)C.C1C=CC=CC=1>[CH3:7][N:8]([CH3:26])[C:9]1[CH:25]=[CH:24][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)=[CH2:5])=[CH:11][CH:10]=1

Komponenten

8

Edukt 5

HCID 6328Methyl iodideHCID 70314,4'-Bis(dimethylamino)benzophenoneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 81995Michler's ethyleneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

After adding 100 ml of benzene to a diethyl ether solution of methylmagnesium iodide prepared from 1.7 g of magnesium, 9.9 g of methyl iodide, and 100 ml of diethyl ether, 16.6 of 4,4'-bis-dimethylaminobenzophenone was gradually added thereto. After stirring at room temperature for 10 hours, the reaction mixture was decomposed by a saturated aqueous ammonium chloride solution, followed by stirring as it was for 2 hours. After separating and water-washing an organic layer, the solvent was distilled off, and the residue was recrystallized from ethanol to obtain 10.7 g of 1,1-bis(4'-dimethylaminophenyl)ethylene. The melting point was 121° to 122° C., and the theoretical yield was 65%.

Aufarbeitung

  1. additionwas gradually added
  2. stirringby stirring as it
  3. waitwas for 2 hours
  4. customAfter separating
  5. washwater-washing an organic layer
  6. distillationthe solvent was distilled off
  7. customthe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-750d9f98b9574c88853959119e9817a8
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04751163

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