4-Isopropylphenol → Bis{4-[4-(propan-2-yl)phenoxy]phenyl}methanone

HRID 370068

Reaktionsgleichung

Reaktionsgleichung von HRID 370068
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+].Br[C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1>CN(C)C=O.[Cu]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:14]2[CH:28]=[CH:27][C:17]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:10][C:7]4[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=4)=[CH:22][CH:21]=3)=[O:19])=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 74654-IsopropylphenolHCID 24758Sodium hydrideHCID 728684,4'-Dibromobenzophenone

Produkt 1

HCID 22023780Bis{4-[4-(propan-2-yl)phenoxy]phenyl}methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 4-isopropylphenol (20.4 g.) in 30 ml of dimethylformamide was added slowly a slurry of sodium hydride, 60% in mineral oil (6.0 g.) in 150 ml of dimethylformamide. When the reaction was complete, 8.5 g. of 4,4'-dibromobenzophenone and 1.0 g. dendritic copper powder were added and the reaction mixture heated to reflux and held at reflux for 24 hours. The solvent was removed under vacuum and the residue poured into ice-water. The crude product was recrystallized from ethanol to give the desired compound, mp 104-105° C. Structure was confirmed by IR, NMR, C-13 NMR and MS.

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux
  3. temperatureat reflux for 24 hours
  4. customThe solvent was removed under vacuum
  5. additionthe residue poured into ice-water
  6. customThe crude product was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f5d29276d5d444eba5187f32acb58de5
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140385

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