Acetone → Methyl 3,5-diiodo-2-methoxybenzoate

HRID 2360026Notes

Reaction equation

HRID 2360026 reaction equation
O[C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S([O:18][CH3:19])(OC)(=O)=O.[CH3:20]C(C)=O>>[I:11][C:10]1[C:2]([O:18][CH3:19])=[C:3]([CH:7]=[C:8]([I:12])[CH:9]=1)[C:4]([O:6][CH3:20])=[O:5]

Participants

4

Reactant 3

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 86313,5-Diiodosalicylic acid

Product 1

HCID 57419464Methyl 3,5-diiodo-2-methoxybenzoate

Procedure

A mixture of 2-hydroxy-3,5-diiodobenzoic acid (3.9 g, 10.0 mmol) potassium carbonate (4.15 g, 30.0 mmol) and dimethyl sulfate (2.77 g, 22.0 mmol) in acetone (33 ml) was heated at reflux for 16 h, cooled and concentrated. The residue was dissolved in EtOAc and washed with water, brine, dried (Na2SO4), filtered and concentrated to give an off-white solid (4.2 g, quantitative yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2498e969c9004950a573074878c50c3d
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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