4-Chloro-o-xylene → 2,2'-Dichloro-4,4',5,5'-tetramethylbenzophenone

HRID 2072749Notes

Reaction equation

HRID 2072749 reaction equation
[Al+3].[Cl-:2].[Cl-:3].[Cl-].Cl[C:6]1[CH:7]=[C:8]([CH3:13])[C:9]([CH3:12])=[CH:10][CH:11]=1.[C:14](Cl)(=[O:18])[C:15](Cl)=O>C(=S)=S>[Cl:2][C:11]1[CH:10]=[C:9]([CH3:12])[C:8]([CH3:13])=[CH:7][C:6]=1[C:14]([C:15]1[CH:10]=[C:9]([CH3:12])[C:8]([CH3:13])=[CH:7][C:6]=1[Cl:3])=[O:18]

Participants

5

Reactant 3

HCID 328864-Chloro-o-xyleneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 150271722,2'-Dichloro-4,4',5,5'-tetramethylbenzophenoneYield 67.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

146 g of AlCl3 are added to a solution of 140 g of 4-chloro-o-xylene and 68 g of oxalyl chloride in 500 ml of CS2 at 0°-5° C. in the course of 2 hours, with stirring. After 20 hours, the mixture is poured onto ice and extracted with 600 ml of CHCl3. The extract is washed with water, dried and evaporated completely. Recrystallisation of the residue from diisopropyl ether gives 103.8 g of 2,2'-dichloro-4,4',5,5'-tetramethylbenzophenone (D).

Workup

  1. additionthe mixture is poured onto ice
  2. extractionextracted with 600 ml of CHCl3
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated completely
  6. customRecrystallisation of the residue from diisopropyl ether

Sources & evidence

ORD record
ord-ba687db4b12c4e2fbe314b51c094cf67
Source dataset
uspto-grants-1990_04
Patent number
US04914182

Reaction notes

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