4-Chloro-o-xylene → HCID 18696680, compound

HRID 1870642Notes

Reaction equation

HRID 1870642 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([CH3:8])=[CH:6][CH:7]=1.[CH3:10][C:11]([CH3:18])([C:15](Cl)=[O:16])[C:12](Cl)=[O:13].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([CH3:8])=[C:6]2[C:7]=1[C:15](=[O:16])[C:11]([CH3:18])([CH3:10])[C:12]2=[O:13]

Participants

5

Reactant 3

HCID 328864-Chloro-o-xyleneHCID 4523180Dimethylmalonyl DichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18696680HCID 18696680, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 35.5 ml of 4-chloro-o-xylene and 29.84 g of dimethylmalonyl chloride in 150 ml of dry dichloromethane was added slowly 34.7 g of AlCl3 under the current of nitrogen gas at -10° C. The reaction mixture was stirred at room temperature for 2 hours, quenched with 200 g of ice, and separated the organic layer. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography to afford 34.99 g of the title compound as yellow solid.

Workup

  1. customquenched with 200 g of ice
  2. customseparated the organic layer
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-b3f21784b0d7430d8b970bda37694360
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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