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

HRID 1292325Notes

Reaction equation

HRID 1292325 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-44d3298dda4c4933925122663bb18245
Source dataset
uspto-grants-1998_05
Patent number
US05756581

Reaction notes

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