Iodoethane → 2-Ethoxy-4-(trifluoromethyl)benzaldehyde

HRID 1816660Notes

Reaction equation

HRID 1816660 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].[CH2:14](I)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:14]([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])[CH3:15]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 224939012-Hydroxy-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 224943382-Ethoxy-4-(trifluoromethyl)benzaldehydeYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

0.80 g of 2-hydroxy-4-(trifluoromethyl)benzaldehyde was dissolved in 8 ml dimethylformamide, and 0.78 g of ethyl iodide and 0.69 g of potassium carbonate were added, and the mixture was stirred at 70° C. for 2 hours. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was successively washed with 1N hydrochloric acid and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (5:1), 0.60 g of 2-ethoxy-4-(trifluoromethyl)benzaldehyde was obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with 1N hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. washfrom fractions eluted with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-3ab593fd741744e0a05f036f523515f4
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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