Methane, dichloromethoxy- → HCID 12629035, compound

HRID 1743382Notes

Reaction equation

HRID 1743382 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([CH3:11])[C:4]=1[CH3:12].[CH3:13][O:14]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:10][O:9][C:6]1[C:5]([CH3:11])=[C:4]([CH3:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH:13]=[O:14]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 148299Benzene, 1,4-dimethoxy-2,3-dimethyl-

Product 1

HCID 12629035HCID 12629035, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dimethoxy-2,3-dimethylbenzene (100 g, 0.60 mol) and dichloromethyl methyl ether (65 mL, 0.72 mol) in dichloromethane (400 mL) was added dropwise titanium tetrachloride (IV)(100 mL, 0.91 mol) over 30 minutes under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was poured into ice (1 kg), the organic layer was separated, and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were washes with water and saturated brine, passed through sodium sulfate-silica gel, dried (eluted with hexane-ethyl acetate 5:1) and concentrated under reduced pressure. The residue was recrystallized from hexane to obtain 107 g of the title compound.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with dichloromethane
  4. customdried
  5. wash(eluted with hexane-ethyl acetate 5:1)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-d8753d3c3fb2443b9f7096f86d374306
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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