Methane, dichloromethoxy- → 2,2,4,6,7-Pentamethyl-2,3-dihydro-1H-indene-5-carbaldehyde

HRID 1870627Notes

Reaction equation

HRID 1870627 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:10][C:9]2[C:4](=[C:5]([CH3:13])[C:6]([CH3:12])=[CH:7][C:8]=2[CH3:11])[CH2:3]1.C[O:16][CH:17](Cl)Cl>ClCCl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:14])[CH2:10][C:9]2[C:4](=[C:5]([CH3:13])[C:6]([CH3:12])=[C:7]([CH:17]=[O:16])[C:8]=2[CH3:11])[CH2:3]1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 148388462,2,4,5,7-Pentamethyl-2,3-dihydro-1H-indene

Product 1

HCID 137335152,2,4,6,7-Pentamethyl-2,3-dihydro-1H-indene-5-carbaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 24.5 g of the 2,2,4,6,7-pentamethylindane in 100 ml of dry dichloromethane was continuously added 18.5 ml of α,α-dichloromethyl methyl ether and 17.6 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 26.8 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-8250cbdbe61f488bb861c6592826dc7b
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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