Reaction #1973967

Reaction equation

2-hydroxy-3,5-diiodobenzoic acid

dimethyl sulfate

acetone

→

solid

methyl 3,5-diiodo-2-methoxybenzoate

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 16 h
3. 3
   Temperaturecooled
4. 4
   Concentrationconcentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
6. 6
   Washwashed with water, brine
7. 7
   Dryingdried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated

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).

Source