Dimethylformamide → HCID 22494013, compound

HRID 1816656Notes

Reaction equation

HRID 1816656 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](O)[CH:3]=1.[CH2:12](I)[CH3:13].[C:15](=O)([O-])[O-].[K+].[K+].CN(C)[CH:23]=[O:24]>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:12][CH3:13])=[O:7])=[C:4]([O:24][CH2:23][CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 787824-Chlorosalicylic acid

Product 1

HCID 22494013HCID 22494013, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

5.0 g of 4-chloro-2-hydroxybenzoic acid was dissolved in 25 ml dimethylformamide, and 14.5 g of ethyl iodide and 12 g of potassium carbonate were added thereto, followed by stirring at 70° C. for 8 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 (2:1), 3.8 g of ethyl 4-chloro-2-ethoxybenzoate 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 (2:1)

Sources & evidence

ORD record
ord-13672613756e4ca7a67eedb6eda20735
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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