Water → 4-Propyl-4'-(1-propynyl)tolan

HRID 465887

Reaktionsgleichung

Reaktionsgleichung von HRID 465887
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:12]([C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1)#[C:13][CH3:14].O>C(NCC)C.[Cu](I)I>[CH2:12]([C:15]1[CH:20]=[CH:19][C:18]([C:11]#[C:10][C:7]2[CH:6]=[CH:5][C:4]([C:1]#[C:2][CH3:3])=[CH:9][CH:8]=2)=[CH:17][CH:16]=1)[CH2:13][CH3:14]

Komponenten

6

Edukt 3

HCID 962WaterHCID 27751331-Ethynyl-4-propylbenzeneHCID 121767134-(1-Propynyl)iodobenzene

Produkt 1

HCID 867461874-Propyl-4'-(1-propynyl)tolan

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8021DiethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4-Propylphenylacetylene (7.21 g, 0.05 mol) and 4-(1-propynyl)iodobenzene (12.1 g, 0.05 mol) were dissolved in diethylamine (30 cc), and then copper iodide (0.29 g, 1.5 mmol) and dichlorobistriphenylphosphinepalladium dichloride (0.53 g, 0.75 mmol) were added. The resulted mixture was reacted with stirring in nitrogen gas current at about 20° C. for 8 hours. After completion of the reaction, water (100 ml) was added to the resulting reaction mixture. The resulting deposited mass was extracted with toluene (50 ml). The resulting toluene solution was washed with dilute hydrochloric acid, followed by water until the washing water became neutral. The resulting material was dried over anhydrous sodium sulfate. Toluene was distilled off from the toluene solution. The residue was then dissolved in a mixed solvent of n-hexane/methylene chloride (1 vol./1 vol.). The solution was subjected to column chromatography using silica gel as a fixed phase, and using the above mixed solvent as an eluent. Fractions showing a single spot were collected by TLC and the mixed solvent was distilled. The residue after distillation was recrystallized from ethyl alcohol (20 ml) to obtain the objective 4-propyl-4'-(1-propynyl)tolan (compound No. 1) (6.7 g). This compound exhibited liquid crystal phases (CI point: 87.7° C., NI point: 85.1° C.).

Aufarbeitung

  1. customThe resulted mixture was reacted
  2. additionwas added to the resulting reaction mixture
  3. extractionwas extracted with toluene (50 ml)
  4. washThe resulting toluene solution was washed with dilute hydrochloric acid
  5. dry with materialThe resulting material was dried over anhydrous sodium sulfate
  6. distillationToluene was distilled off from the toluene solution
  7. dissolutionThe residue was then dissolved in a mixed solvent of n-hexane/methylene chloride (1 vol./1 vol.)
  8. customwere collected by TLC
  9. distillationthe mixed solvent was distilled
  10. distillationThe residue after distillation
  11. customwas recrystallized from ethyl alcohol (20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-17f8ee4ead804edaa465a8926f0868e6
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05154851

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