Methanol → Methyl 2-iodo-4-methoxybenzoate

HRID 1075823Notes

Reaction equation

HRID 1075823 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 l. methanol and 400 ml. of concentrated sulfuric acid are heated at reflux for 4 hours. The solution is then evaporated under reduced pressure, treated with water, and extracted with ether. The organic phase is then washed with aqueous sodium thiosulfate solution and aqueous sodium bicarbonate solution and subsequently dried over sodium sulfate. The solution is filtered, evaporated under reduced pressure and distilled. There is obtained the 2-iodo-4-methoxy-benzoic acid methyl ester, having a boiling point of 95°-98°/0.04 mm.

Workup

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

Sources & evidence

ORD record
ord-2e50be6389b74ac4b4d3a338ca5a6be5
Source dataset
uspto-grants-1976_05
Patent number
US03954769

Reaction notes

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