Water → 2-methoxy-3,5-dimethylbenzaldehyde

HRID 2228660Notes

Reaction equation

HRID 2228660 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH3:10].[CH3:11][O:12][CH:13](Cl)Cl.O>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:11][O:12][C:13]1[C:4]([CH3:10])=[CH:5][C:6]([CH3:9])=[CH:7][C:8]=1[CH:3]=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 812212,4-Dimethylanisole

Product 1

HCID 47704302-methoxy-3,5-dimethylbenzaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methoxy-2,4-dimethylbenzene (8.00 g, 58.7 mmol) and 1,1-dichloromethyl methyl ether (7.40 g, 64.7 mmol) in methylene chloride (30 mL) was added titanium tetrachloride (20.0 g, 105 mmol) at 0° C. and the mixture was stirred at that temperature for 20 minutes. This reaction mixture was poured into iced water and the organic layer was taken, washed with saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide 9.40 g of the title compound. Yield 98%.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d9125390289941279b968d39412b0d5e
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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