Nitrobenzene → 2-p-Methoxyphenyl-3-(3',5'-dimethylbenzoyl)benzofuran

HRID 1414610Notes

Reaction equation

HRID 1414610 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[CH:26]=2)=[CH:18][CH:17]=1.[CH3:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([CH3:41])[CH:40]=1)[C:35](Cl)=[O:36]>O>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[C:26]=2[C:35](=[O:36])[C:34]2[CH:38]=[C:39]([CH3:41])[CH:40]=[C:32]([CH3:31])[CH:33]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 810883,5-Dimethylbenzoyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 107278342-(4-Methoxyphenyl)benzofuran

Product 1

HCID 214879222-p-Methoxyphenyl-3-(3',5'-dimethylbenzoyl)benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (0°) solution of 14.0 g. (0.105 mol.) of aluminum chloride in 100 ml. of nitrobenzene was added 11.2 g. (0.05 mol.) of 2-p-methoxyphenylbenzofuran followed immediately by 10.0 g. (0.06 mol.) of 3,5-dimethylbenzoyl chloride. The reaction mixture was stirred at 0° for 12 minutes (until the red color began to turn reddish-brown) then poured into water. The aqueous mixture was steam distilled to remove nitrobenzene and the residue was dissolved in methylene chloride. The methylene chloride solution was washed with aqueous sodium carbonate and saturated sodium chloride solution, dried (MgSO4) and concentrated at reduced pressure to give a residue which was purified by column chromatography to give 2-p-methoxyphenyl-3-(3',5'-dimethylbenzoyl)benzofuran which was then crystallized from ethanol.

Workup

  1. temperatureTo a cooled (0°) solution of 14.0 g
  2. distillationdistilled
  3. customto remove nitrobenzene
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washThe methylene chloride solution was washed with aqueous sodium carbonate and saturated sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated at reduced pressure
  8. customto give a residue which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b236f47d427942899310ac25fa918b41
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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