1,4-Dichlorobenzene → (2,5-Dichlorophenyl)(3-methylphenyl)methanone

HRID 248656Notes

Reaction equation

HRID 248656 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7](Cl)=[O:8])[CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[C:7]([C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=1)=[O:8]

Participants

4

Reactant 3

HCID 46851,4-Dichlorobenzene2×HCID 743753-Methylbenzoyl chloride2×HCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 18704036(2,5-Dichlorophenyl)(3-methylphenyl)methanoneYield 53%

Procedure

The procedure of Example 2 was followed, using 22 ml (0.17 mol) of 3-toluoyl chloride and 60 g (0.45 mol) of aluminum chloride in 120 g (0.82 mol) of 1,4-dichlorobenzene. (The molar ratio of reactants was 2.6:4.8:1.0 (AlCl3 :Dichlorobenzene:3-Toluoyl Chloride)). Pure 2,5-dichloro-3'-methyl-benzophenone was isolated in 53% yield after the crude product was recrystallized twice from hexane.

Sources & evidence

ORD record
ord-2624c3d956854183a95148f8c3cc395b
Source dataset
uspto-grants-1993_05
Patent number
US05210313

Reaction notes

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