Water → 4-Chlorophenyl 2-chloro-4-nitrophenyl ketone

HRID 1361468Notes

Reaction equation

HRID 1361468 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 7964ChlorobenzeneHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 8862964-Chlorophenyl 2-chloro-4-nitrophenyl ketoneYield 81%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

2-Chloro-4-nitrobenzoyl chloride (23.1 g) was added dropwise to a mixture composed of 11.8 g of monochlorobenzene and 13.3 g of aluminum chloride. The mixed solution was stirred with heating at 40° C. for 6 hr and was then added dropwise to 45 mL of warm water. Further, toluene and ethyl acetate were added to the mixed solution followed by separation and washing with sodium bicarbonate water and brine. The organic layer was concentrated under the reduced is pressure. n-Hexane was added to the residue, and the precipitated crystals were collected by filtration to give 24.0 g of (2-chloro-4-nitrophenyl)-(4′-chlorophenyl)methanone (yield 81%).

Workup

  1. customfollowed by separation
  2. washwashing with sodium bicarbonate water and brine
  3. concentrationThe organic layer was concentrated under the
  4. additionn-Hexane was added to the residue
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-d285c06ed4064fc0ad00f373a94416af
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

Loading…