Hydrochloric Acid → (2,5-Dichlorophenyl)(3-methylphenyl)methanone

HRID 481736

Reaction equation

HRID 481736 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7](Cl)=[O:8])[CH:2]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>CCOCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[C:7]([C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 46851,4-DichlorobenzeneHCID 743753-Methylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of m-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. Hydrogen chloride started to evolve from the solution. 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 20 g of white crystals (53%).

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-2e41397699cf4c699a6c40d3e1fbf90b
Source dataset
uspto-grants-1998_08
Patent number
US05789521

Linked notes

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