Iodoethane → HCID 22494230, compound

HRID 1816650Notes

Reaction equation

HRID 1816650 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[CH2:13](I)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 22494230HCID 22494230, compoundYield 632.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.25 g of methyl 2-chloro-4-hydroxybenzoate was dissolved in 10 ml dimethylformamide, and 0.23 g of ethyl iodide and 0.21 g of potassium carbonate were added, and the mixture was stirred for 8 hours. After diluting the reaction mixture, it was 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 dissolved in 6 ml methanol, and 3 ml of 1 N sodium hydroxide was added, and the solution was stirred at room temperature for 6 hours. The reaction mixture was ice-cooled and neutralized with 1N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was evaporated, to give 1.7 g of 2-chloro-4-ethoxybenzoic acid.

Workup

  1. additionAfter diluting the reaction mixture, it
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was successively washed with 1N hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in 6 ml methanol
  7. addition3 ml of 1 N sodium hydroxide was added
  8. stirringthe solution was stirred at room temperature for 6 hours
  9. temperaturecooled
  10. extractionby extracting with ethyl acetate
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5a2d22ada4c0498fa5cc6cd0f0c05dc8
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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