Hydrochloric Acid → 4-[4-(4-Chlorobenzoyl)benzyl]-3,5-dichloronitrobenzene

HRID 1602880Notes

Reaction equation

HRID 1602880 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[CH2:15]([C:22]1[C:27]([Cl:28])=[CH:26][C:25]([N+:29]([O-:31])=[O:30])=[CH:24][C:23]=1[Cl:32])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>ClCCl.C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][C:22]3[C:27]([Cl:28])=[CH:26][C:25]([N+:29]([O-:31])=[O:30])=[CH:24][C:23]=3[Cl:32])=[CH:17][CH:18]=2)=[O:11])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 216993324-Benzyl-3,5-dichloronitrobenzene

Product 1

HCID 196083034-[4-(4-Chlorobenzoyl)benzyl]-3,5-dichloronitrobenzene

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent3×

Procedure

In 15 ml of dichloromethane was suspended 1.30 g of AlCl3, and a solution of 1.43 g of 4-chlorobenzoyl chloride in 3 ml of dichloromethane was added to the suspension for a period of 30 minutes. A solution of 2.00 g of 4-benzyl-3,5-dichloronitrobenzene in 2 ml of dichloromethane was added for a period of 15 minutes, and the reaction mixture was refluxed for 22 hours. The reaction mixture was poured into 25 ml of ice-water, and 30 ml of chloroform and 3 ml of conc. hydrochloric acid were added. The resulting mixture was stirred for 15 minutes at a room temperature, and the organic layer was separated, washed with water and saturated aqueous sodium bicarbonate solution, dried and concentrated to quantitatively give the above-identified compound as oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 22 hours
  2. additionwere added
  3. customthe organic layer was separated
  4. washwashed with water and saturated aqueous sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ebeafb0c8418424b88859342b75ee177
Source dataset
uspto-grants-1999_11
Patent number
US05985875

Reaction notes

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