Water → 4-methoxy-3-(methoxymethoxy)benzaldehyde

HRID 1352849Notes

Reaction equation

HRID 1352849 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20]Cl.O>CN(C)C=O>[CH3:9][O:8][C:7]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH2:18][O:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 6401524-methoxy-3-(methoxymethoxy)benzaldehydeYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of isovanillin (5.00 g, 32.9 mmol) in N,N-dimethylformamide (300 ml) were added potassium carbonate (5.00 g, 36.1 mmol) and chloromethyl methyl ether (2.91 g, 36.1 mmol), and the mixture was stirred for 4 hours at 50° C. The mixture was allowed to cool to room temperature, followed by addition of water. The mixture was extracted with ethyl acetate-toluene (3:1). The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography (hexane:ethyl acetate=3:1) to give the subject compound (5.80 g, 89.9%).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate-toluene (3:1)
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-df5ab24ce82c4f78baeddf35becc286b
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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