Diethylamine → HCID 14716807, Verbindung

HRID 1655139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1655139
I[C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C(N[CH2:12][CH3:13])C.[CH2:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)[CH2:15][CH3:16]>[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:21]([C:2]1[CH:7]=[CH:6][C:5]([C:24]#[C:23][C:20]2[CH:19]=[CH:18][C:17]([C:14]#[C:15][C:16]3[CH:19]=[CH:18][C:17]([CH2:22][CH2:12][CH3:13])=[CH:14][CH:15]=3)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1)[CH2:20][CH3:23]

Komponenten

7

Edukt 3

HCID 8021DiethylamineHCID 12208p-DiiodobenzeneHCID 27751331-Ethynyl-4-propylbenzene

Produkt 1

HCID 14716807HCID 14716807, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

1,4-Diiodobenzene (2.5 g, 7.57 mmol) was added to diethylamine (80 ml) in nitrogen gas stream, followed by agitating the mixture at room temperature, successively adding copper iodide (60 mg) and dichlorobis(triphenylphosphine)palladium(II) (100 mg), adding 4-propylphenylacetylene (4.37 g, 30 mmol) in several steps, agitating the reaction mixture at room temperature overnight, adding water (200 ml), extracting the resulting deposited crystals with toluene (100 ml), washing the toluene solution with dilute hydrochloric acid, water, an aqueous solution of sodium hydrogen sulfate and water in this order, drying the solution on anhydrous sodium sulfate, passing it through a short column of activated alumina, distilling off toluene and recrystallizing the residue from ethyl acetate to obtain the objective 1,4-bis-(4-propylphenyl-ethynyl)benzene (1.92 g, 5.3 mmol). This product exhibited liquid crystal phases. C-N point: 179.1° C. N-I point: 245.5° C.

Aufarbeitung

  1. stirringagitating the reaction mixture at room temperature overnight
  2. extractionextracting the resulting
  3. washwashing the toluene solution with dilute hydrochloric acid, water
  4. dry with materialan aqueous solution of sodium hydrogen sulfate and water in this order, drying the solution on anhydrous sodium sulfate
  5. distillationdistilling off toluene
  6. customrecrystallizing the residue from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ac8d1be914834fbd90fab20fe68ec7cf
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250216

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