Methane, dichloromethoxy- → HCID 18696710, compound

HRID 1870638Notes

Reaction equation

HRID 1870638 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[CH:3]=1.[CH3:16][O:17]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]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[C:3]=1[CH:16]=[O:17]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 18696677HCID 18696677, compound

Product 1

HCID 18696710HCID 18696710, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 19 g of the 6-chloro-2-ethyl-2,4,7-trimethylindane in 100 ml of dry dichloromethane was continuously added 9.5 ml of α,α-dichloromethyl methyl ether and 11.5 ml of TiCl4 at 0° C. The reaction mixture was stirred at room temperature for 2 hours, quenched with 100 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 20.85 g of the title compound as yellow solid.

Workup

  1. customat 0° C
  2. customquenched with 100 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-3d23d6e81d92420da97a418367afcd9a
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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