1,4-Dichlorobenzene → 2,5-Dichloro-2'-methylbenzophenone

HRID 264589Notes

Reaction equation

HRID 264589 reaction equation
[C:1]1([CH3:10])[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>CCOCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 46851,4-DichlorobenzeneHCID 702762-Methylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 187040332,5-Dichloro-2'-methylbenzophenoneYield 36%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of o-toluoyl chloride (22 g, 0.17 mol) and 1,4-dichlorobenzene (120 g, 0.82 mol) was heated to 100° C. in a flask. Aluminum chloride (60 g, 0.45 mol) was added in one portion. The mixture was heated to 170° C. in 30 min and stirred at this temperature for 3 hours. The resulting brownish solution was cooled to about 80° C. and poured onto ice. Ether (50 ml) was added. The organic layer was separated and distilled under vacuum after the removal of ether. The residue from distillation was recrystallized twice from hexane to give 16 g of white crystals (36%).

Workup

  1. temperatureThe mixture was heated to 170° C. in 30 min
  2. temperatureThe resulting brownish solution was cooled to about 80° C.
  3. additionpoured onto ice
  4. customThe organic layer was separated
  5. distillationdistilled under vacuum
  6. customafter the removal of ether
  7. distillationThe residue from distillation
  8. customwas recrystallized twice from hexane

Sources & evidence

ORD record
ord-8d0a4bf60f9549059596681299f2d312
Source dataset
uspto-grants-1997_07
Patent number
US05646232

Reaction notes

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