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

HRID 370068

Reaction equation

HRID 370068 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f5d29276d5d444eba5187f32acb58de5
Source dataset
uspto-grants-2000_10
Patent number
US06140385

Linked notes

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