Potassium Iodide → [1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-

HRID 442588

Reaktionsgleichung

Reaktionsgleichung von HRID 442588
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Produkt 1

HCID 112405[1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 4-cyano-4'-hydroxybiphenyl (56) (10.10 g, 0.052 mol), 1-bromodecane (14.38 g, 0.065 mol), anhydrous potassium carbonate (37.32 g, 0.27 mol), butanone (300 ml) and a trace of potassium iodide was heated under reflux overnight. The cooled solution was filtered to remove inorganic salts and the solvent was removed in vacuo. The residual oil was distilled (to remove excess bromide) and finally purified by column chromatography (dichloromethane) to yield a colourless, low melting solid.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. filtrationThe cooled solution was filtered
  3. customto remove inorganic salts
  4. customthe solvent was removed in vacuo
  5. distillationThe residual oil was distilled
  6. custom(to remove excess bromide)
  7. customfinally purified by column chromatography (dichloromethane)
  8. customto yield a colourless,

Quellen und Nachweise

ORD-Eintrag
ord-62ba16d6b6194f72842bd59dca9816a2
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891358

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