Sodium Iodide → 3-Hydroxy-4-iodobenzoic acid

HRID 250915Notes

Reaction equation

HRID 250915 reaction equation
[OH-].[Na+].[I-:3].[Na+].[OH:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10].Cl[O-].[K+]>CO>[OH:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[I:3])[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 74203-Hydroxybenzoic AcidHCID 14798Sodium HydroxideHCID 23665762Potassium hypochlorite

Product 1

HCID 7368543-Hydroxy-4-iodobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

21.0 g (0.52 mol, 1.05 eq) of sodium hydroxide and then 78.7 g (0.52 mol, 1.05 eq) of sodium iodide are added to a solution of 69.1 g (0.5 mol, 1 eq) of 3-hydroxybenzoic acid in 700 ml of methanol. The reaction mixture is cooled to 0° C. and potassium hypochlorite solution (0.52 mol, 1.05 eq) is then added dropwise. The reaction medium is stirred at 0-5° C. for 2 hours and then at room temperature overnight. The methanol is evaporated off and the reaction medium is then acidified with concentrated hydrochloric acid solution. The precipitated product is filtered off, washed with water and dried. 121 g of 3-hydroxy-4-iodobenzoic acid are obtained in the form of an off-white solid. Yield=92%

Workup

  1. customat room temperature
  2. customovernight
  3. customThe methanol is evaporated off
  4. filtrationThe precipitated product is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8659b4409d0a4f239d22195facf37b3e
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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