Nitrobenzene → 2,4-Dichlorophenyl 4'-methyl-4-biphenylyl ketone

HRID 1645808Notes

Reaction equation

HRID 1645808 reaction equation
[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.[Cl:27][C:28]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>O>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:30]([C:29]3[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:28]=3[Cl:27])=[O:31])=[CH:25][CH:26]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 125664-MethylbiphenylHCID 666452,4-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 197420752,4-Dichlorophenyl 4'-methyl-4-biphenylyl ketoneYield 66.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

35 mL of nitrobenzene were cooled in an ice bath and then treated in succession with 5.2 g of aluminium chloride and 5.0 g of 4-methylbiphenyl. The mixture was brought to room temperature and then treated slowly with 7.7 g of 2,4-dichlorobenzoyl chloride. The mixture was stirred at room temperature overnight, poured into water and extracted with methylene chloride. The extracts were washed with 2N hydrochloric acid and water, dried over magnesium sulphate and evaporated. The residue was chromatographed on silica gel with toluene/ethyl acetate 9:1. There were obtained 6.7 g (63%) of 2,4-dichlorophenyl 4'-methyl-4-biphenylyl ketone as a colorless solid with a m.p. of 184°-185° C.

Workup

  1. customwas brought to room temperature
  2. extractionextracted with methylene chloride
  3. washThe extracts were washed with 2N hydrochloric acid and water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel with toluene/ethyl acetate 9:1

Sources & evidence

ORD record
ord-f24677eee0264b8180fe8408417a5806
Source dataset
uspto-grants-1993_01
Patent number
US05177067

Reaction notes

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