Methanol → Methyl 2-iodo-4-methoxybenzoate

HRID 1973088Notes

Reaction equation

HRID 1973088 reaction equation
[I:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:2]=1[I:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 128221822-Iodo-4-methoxybenzoic acid

Product 1

HCID 54385122Methyl 2-iodo-4-methoxybenzoate

Procedure

411 G. of 2-iodo-4-methoxy-benzoic acid, 4 liters of methanol and 400 ml. of concentrated sulfuric acid are heated under reflux for 4 hours. The solution is evaporated under reduced pressure, treated with water and extracted with ether. The organic phase is washed successively with aqueous sodium thiosulfate and aqueous sodium bicarbonate and then dried over sodium sulfate. The solution is filtered, evaporated under reduced pressure, distilled, and there is obtained 2-iodo-4-methoxy-benzoic acid methyl ester having a boiling point of 95°-98° C./0.04 mm.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solution is evaporated under reduced pressure
  3. additiontreated with water
  4. extractionextracted with ether
  5. washThe organic phase is washed successively with aqueous sodium thiosulfate and aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution is filtered
  8. customevaporated under reduced pressure
  9. distillationdistilled

Sources & evidence

ORD record
ord-9554eb480ed04482be4d8c3df77f52cf
Source dataset
uspto-grants-1976_12
Patent number
US03996229

Reaction notes

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