Methane, dichloromethoxy- → HCID 18696672, compound

HRID 1870630Notes

Reaction equation

HRID 1870630 reaction equation
[CH2:1]([C:3]1([CH3:15])[CH2:11][C:10]2[C:5](=[C:6]([CH3:14])[CH:7]=[C:8]([CH3:13])[C:9]=2[CH3:12])[CH2:4]1)[CH3:2].[CH3:16][O:17]C(Cl)Cl>ClCCl.Cl[Ti](Cl)(Cl)Cl>[CH2:1]([C:3]1([CH3:15])[CH2:11][C:10]2[C:5](=[C:6]([CH3:14])[C:7]([CH:16]=[O:17])=[C:8]([CH3:13])[C:9]=2[CH3:12])[CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 18696681HCID 18696681, compound

Product 1

HCID 18696672HCID 18696672, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 17.7 g of the 2-ethyl-2,4,5,7-tetramethylindane in 100 ml of dry dichloromethane was continuously added 9.5 ml of α,α-dichloromethyl methyl ether and 11.6 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 18.26 g of the title compound as brown 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-cb3292ef2a0b4e0ea5f1613675744272
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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