Methanol → methyl 2-iodo-3-methoxybenzoate

HRID 859122Notes

Reaction equation

HRID 859122 reaction equation
[I:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:13]O.S(=O)(=O)(O)O>O>[I:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4582192-Iodo-3-methoxybenzoic acid

Product 1

HCID 299486methyl 2-iodo-3-methoxybenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2-iodo-3-methoxybenzoic acid (20 g, 0.07 mol; prepared in a manner similar to that described above), methanol (300 ml) and concentrated sulphuric acid (3.5 ml) was heated under reflux for 8 hours, cooled to ambient temperature and added to water (1500 ml). The product was extracted into dichloromethane (3×500 ml), the combined extracts were washed with 5% aqueous sodium hydroxide solution (3×500 ml), then they were dried (MgSO4) and the solvent was removed in vacuo to give methyl 2-iodo-3-methoxybenzoate (18.5 g, 90%) as a solid, m.pt. 58–61° C.

Workup

  1. customprepared in a manner similar to
  2. temperaturewas heated
  3. temperatureunder reflux for 8 hours
  4. extractionThe product was extracted into dichloromethane (3×500 ml)
  5. washthe combined extracts were washed with 5% aqueous sodium hydroxide solution (3×500 ml)
  6. dry with materialthey were dried (MgSO4)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bc7e70cf9ab0488bb589964f4e0ffe8c
Source dataset
uspto-grants-2006_12
Patent number
US07151102B2

Reaction notes

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