Methyl iodide → 4-Chloro-3-hydroxy-5-methoxy-benzoic Acid Methyl Ester

HRID 1831819Notes

Reaction equation

HRID 1831819 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([Cl:11])=[C:6]([OH:12])[CH:5]=1.[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:14])[C:7]([Cl:11])=[C:6]([OH:12])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69652313HCID 69652313, compound

Product 1

HCID 696522944-Chloro-3-hydroxy-5-methoxy-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.9 g (19.3 mmol) of 4-Chloro-3,5-dihydroxy-benzoic acid methyl ester was dissolved in 250 ml of DMF and treated at 0° C. with 8.6 g (62 mmol) of potassium carbonate and 2.72 g (19.2 mmol) of iodomethane. The reaction solution was stirred at RT for 16 h. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and this solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with sodium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (5/1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthis solution was washed three times with water
  3. dry with materialThe organic phase was dried with sodium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (5/1)

Sources & evidence

ORD record
ord-07ff7d9de4ff4f1798d06d693292b3fe
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

Loading…