Nitrobenzene → HCID 19043690, compound

HRID 1900132Notes

Reaction equation

HRID 1900132 reaction equation
[N+](C1C=CC=CC=1)([O-])=[O:2].[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:33]=[CH:34][C:35]=1[Cl:36])[CH2:31]Cl>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:33]=[CH:34][C:35]([Cl:36])=[C:28]([Cl:27])[CH:29]=3)=[O:2])=[CH:25][CH:26]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 76093,4-Dichlorobenzyl chlorideHCID 125664-MethylbiphenylHCID 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-methyl-biphenyl. The mixture is brought to room temperature and then treated with 7.7 g of 3,4-dichlorobenzyl 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. 3,4Dichlorophenyl 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-95a1499e9b8648be91f5c6de272d8f24
Source dataset
uspto-grants-1996_11
Patent number
US05574071

Reaction notes

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