Sodium Iodide → 3-Hydroxy-4-iodobenzoic acid

HRID 390623

Reaction equation

HRID 390623 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-].[Na+]>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 23665760Sodium Hypochlorite

Product 1

HCID 7368543-Hydroxy-4-iodobenzoic acidYield 31.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

21 g (520 mmol) of sodium hydroxide and then 78.7 g (520 mmol) of sodium iodide are added to a solution of 69 g (500 mmol) of 3-hydroxybenzoic acid in 700 mL of methanol. The reaction mixture is cooled to 0° C. and aqueous sodium hypochlorite solution is then added (520 mmol). 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. 41.92 g of 3-hydroxy-4-iodobenzoic acid are obtained in the form of an off-white solid. The aqueous phase is extracted with ethyl acetate, dried over magnesium sulfate, filtered and evaporated and the residue obtained is taken up in heptane and then filtered.

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-e3f504ac44c9462b9c0bd6996b66d575
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Linked notes

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