Nitrobenzene → HCID 19043690, compound

HRID 2397043Notes

Reaction equation

HRID 2397043 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:29]=[C:30]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:31](Cl)=[O:32]>O>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:31]([C:30]3[CH:34]=[CH:35][C:36]([Cl:37])=[C:28]([Cl:27])[CH:29]=3)=[O:32])=[CH:25][CH:26]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 125664-MethylbiphenylHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 19043690HCID 19043690, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

35 ml of nitrobenzene are cooled in an ice-bath and then treated in succession with 5.2 g of aluminum chloride and 5.0 g of 4-methylbiphenyl. The mixture is brought to room temperature and then treated with 7.7 g of 3,4-dichlorobenzoyl chloride. The mixture is stirred at room temperature, poured into water and extracted with methylene chloride. The extracts are washed with 2N hydrochloric acid and water, dried over magnesium sulfate and evaporated. The residue is chromatographed on silica gel with toluene/ethyl acetate 9:1. 3,4-Dichlorophenyl 4'-methyl-4-biphenylyl ketone is obtained.

Workup

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

Sources & evidence

ORD record
ord-e220c7d29f6f431a88f026bb39316816
Source dataset
uspto-grants-1996_02
Patent number
US05495048

Reaction notes

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