Water → 2-Methoxy-4-(trifluoromethyl)benzaldehyde

HRID 1816566Notes

Reaction equation

HRID 1816566 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH3:16]I.O>CN(C)C=O>[CH3:16][O:1][C:2]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 224939012-Hydroxy-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.5 g of 2-hydroxy-4-(trifluoromethyl)benzaldehyde was dissolved in 20 ml N,N-dimethylformamide. 1.0 g of sodium hydride (60% oily) was added, followed by stirring at room temperature for 30 minutes. 1.8 ml methyl iodide was added dropwise thereinto, follwed by reacting for 1 hour. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, to give 3.0 g of 2-methoxy-4-(trifluoromethyl)benzaldehyde as a colorless oil from fractions eluted with hexane-ethyl acetate (9:1).

Workup

  1. waitby reacting for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-579f684506d24b669ca983c4a6311cf4
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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