Methyl iodide → 2-Chloro-4-hydroxy-benzoic acid methyl ester

HRID 1816649Notes

Reaction equation

HRID 1816649 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CI.[C:14](=O)(O)[O-].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 918212-Chloro-4-hydroxybenzoic acidHCID 516893Potassium Bicarbonate

Product 1

HCID 134988302-Chloro-4-hydroxy-benzoic acid methyl esterYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.9 g of 2-chloro-4-hydroxybenzoic acid was dissolved in 20 ml dimethylformamide, and 1.8 g of methyl iodide and 1.2 g of potassium bicarbonate were added, and the mixture was stirred at room temperature for 3 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 (3:1), 1.7 g of methyl 2-chloro-4-hydroxybenzoate 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 (3:1)

Sources & evidence

ORD record
ord-b1c3724260864ce1accf0ad50a98bda5
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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