Methanol → Methyl 3-hydroxy-4-iodobenzoate

HRID 250916Notes

Reaction equation

HRID 250916 reaction equation
S(=O)(=O)(O)O.C[C:7]1[C:15]([OH:16])=[C:14]([I:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:18]O>>[OH:16][C:15]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[I:17])[C:9]([O:11][CH3:18])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 67272847HCID 67272847, compound

Product 1

HCID 10378812Methyl 3-hydroxy-4-iodobenzoateYield 70%

Procedure

59 ml (1.10 mol, 2.4 eq) of sulfuric acid are added to a solution of 121 g (0.458 mol, 1 eq) of methyl 3-hydroxy-4-iodobenzoic acid in 700 ml of methanol. The reaction mixture is refluxed for 6 days. The methanol is evaporated off and the reaction medium is then poured into water and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is concentrated and the solid obtained is filtered off and dried. 88.56 g of methyl 3-hydroxy-4-iodobenzoate are obtained in the form of white crystals. Yield=70%

Workup

  1. temperatureThe reaction mixture is refluxed for 6 days
  2. customThe methanol is evaporated off
  3. additionthe reaction medium is then poured into water
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe solvent is concentrated
  8. customthe solid obtained
  9. filtrationis filtered off
  10. customdried

Sources & evidence

ORD record
ord-f09ffa3dd5304a168382303d746db7f9
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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