5-Iodosalicylic acid → HCID 14939514, compound

HRID 1280444Notes

Reaction equation

HRID 1280444 reaction equation
[I:1][C:2]1[CH:10]=[C:6](C(O)=O)[C:5]([OH:11])=[CH:4][CH:3]=1>CO.S(=O)(=O)(O)O>[CH3:3][CH2:4][C:5]([O:11][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:10][CH:6]=1)=[O:11]

Participants

4

Reactant 1

HCID 83885-Iodosalicylic acid

Product 1

HCID 14939514HCID 14939514, compoundYield 133.9%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-iodosalicylic acid (5.0 g, 18.94 mmol) in methanol (100 mL) was added a few drops of sulfuric acid. The reaction was stirred at reflux for 24 hours. The reaction solvent (methanol) was evaporated to small volume and water was added and extracted with dichloromethane. The organic layer was washed with 10% NaHCO3 solution, water and brine, dried over magnesium sulfate, filtered and evaporated to give the title compound (3.5 g, 66.5%): 1H NMR (CDCl3) δ 3.96 (s, 3H), 6.78 (d, 1H), 7.70 (dd, 1H), 8.12 (d, 1H).

Workup

  1. temperatureat reflux for 24 hours
  2. customThe reaction solvent (methanol) was evaporated to small volume and water
  3. additionwas added
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with 10% NaHCO3 solution, water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b20c16eec8d245aba82c519ede12f8b9
Source dataset
uspto-grants-2002_09
Patent number
US06451801B1

Reaction notes

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