Methane, dichloromethoxy- → HCID 18696675, compound

HRID 1870633Notes

Reaction equation

HRID 1870633 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8]2)=[C:4]([CH3:14])[CH:3]=1.[CH3:15][O:16]C(Cl)Cl>ClCCl.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH3:12])([CH3:13])[CH2:8]2)=[C:4]([CH3:14])[C:3]=1[CH:15]=[O:16]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 18696714HCID 18696714, compound

Product 1

HCID 18696675HCID 18696675, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 19.8 g of the 6-chloro-2,2,4,7-tetramethylindane in 100 ml of dry dichloromethane was continuously added 13 ml of α,α-dichloromethyl methyl ether and 12.4 ml of TiCl4 at 0° C. The reaction mixture was stirred at room temperature for 2 hours, quenched with 200 ml of water, and separated the organic layer. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography to afford 21.8 g of the title compound as yellow solid.

Workup

  1. customat 0° C
  2. customquenched with 200 ml of water
  3. customseparated the organic layer
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-0113b9be8f8d440a96e59f9323d46efc
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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