4-Chloro-o-xylene → 7-Chloro-2-ethyl-2,4,5-trimethylindan-1,3-dione

HRID 1870646Notes

Reaction equation

HRID 1870646 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([CH3:8])=[CH:6][CH:7]=1.[CH2:10]([C:12]([CH3:19])([C:16](Cl)=[O:17])[C:13](Cl)=[O:14])[CH3:11].[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:16](=[O:17])[C:12]([CH2:10][CH3:11])([CH3:19])[C:13]2=[O:14]

Participants

5

Reactant 3

HCID 328864-Chloro-o-xyleneHCID 6451240Aluminum(III) ChlorideHCID 12811039Ethylmethylmalonyl chloride

Product 1

HCID 186967157-Chloro-2-ethyl-2,4,5-trimethylindan-1,3-dioneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 28 ml of 4-chloro-o-xylene and 37.6 g of ethylmethylmalonyl chloride in 300 ml of dry dichloromethane was added slowly 26.7 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 24.67 g of the title compound as a 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-51d40a73279946faa836d2320589220e
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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