Benzene → HCID 18696714, compound

HRID 1870632Notes

Reaction equation

HRID 1870632 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6](=O)[C:7]([CH3:14])([CH3:13])[C:8]2=O)=[C:4]([CH3:16])[CH:3]=1.C1C=CC=CC=1>Cl.C(O)C>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH3:13])([CH3:14])[CH2:8]2)=[C:4]([CH3:16])[CH:3]=1

Participants

5

Reactant 2

HCID 241BenzeneHCID 18696678HCID 18696678, compound

Product 1

HCID 18696714HCID 18696714, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a mixture of 100 g of 7% Zn/Hg in 200 ml of 20% hydrochloric acid and 70ml of ethanol was added 27.32 g of the 6-chloro-2,2,4,7-tetramethylindan-1,3-dione with stirring. After refluxing for 6 hours, the reaction mixture was added 100 ml of benzene and refluxed for 1 hour. The reaction mixture was cooled to room temperature and extracted with diethyl ether. 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 15.67 g of the title compound as yellow oil.

Workup

  1. temperatureAfter refluxing for 6 hours
  2. temperaturerefluxed for 1 hour
  3. extractionextracted with diethyl ether
  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-0cc5a491060f4aef91e102cf56ff36f3
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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