Methanol → Methyl 2-iodo-4-methoxybenzoate

HRID 441988

Reaction equation

HRID 441988 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-78bc88da641e4f408bf2b38b0b3f4b30
Source dataset
uspto-grants-1977_08
Patent number
US04044010

Linked notes

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