Methane, dichloromethoxy- → HCID 18696703, compound

HRID 1870644Notes

Reaction equation

HRID 1870644 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([CH3:13])=[C:6]2[C:10]=1[CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7]2.[CH3:15][O:16]C(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:3]([CH:15]=[O:16])=[C:4]([CH3:14])[C:5]([CH3:13])=[C:6]2[C:10]=1[CH2:9][C:8]([CH3:11])([CH3:12])[CH2:7]2

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 18696713HCID 18696713, compound

Product 1

HCID 18696703HCID 18696703, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17.0 g of the 7-chloro-2,2,4,5-tetramethylindane in 100 ml of dry dichloromethane was continuously added 18.5 ml of α,α-dichloromethyl methyl ether and 11 ml of TiCl2 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 14.7 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-1d95ffc281f749528caba8c49b9aa1dd
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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