Sodium Iodide → 3-Hydroxy-4-iodobenzoic acid

HRID 1361088Notes

Reaction equation

HRID 1361088 reaction equation
Cl[O-].[Na+].[OH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9].[OH-].[Na+].[I-:16].[Na+]>CO>[OH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[I:16])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 74203-Hydroxybenzoic AcidHCID 14798Sodium HydroxideHCID 23665760Sodium Hypochlorite

Product 1

HCID 7368543-Hydroxy-4-iodobenzoic acidYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1319 g (1.52 mol) of commercial 9.6% sodium hypochlorite solution are added dropwise to a solution of 200 g (1.45 mol) of 3-hydroxybenzoic acid, 61 g (1.52 mol) of sodium hydroxide powder and 228 g (1.52 mol) of sodium iodide in 2 l of methanol cooled beforehand to 0° C. The reaction medium is stirred at room temperature for 72 hours. After evaporating off the methanol, the solution is cooled to 10° C. and acidified with aqueous hydrochloric acid solution to pH 2. The mixture is stirred for 2 hours and the product precipitates. The product is filtered off, washed thoroughly with water and dried under vacuum at 50° C. 150 g (39%) of 3-hydroxy-4-iodobenzoic acid are obtained in the form of a white solid.

Workup

  1. customAfter evaporating off the methanol
  2. temperaturethe solution is cooled to 10° C.
  3. stirringThe mixture is stirred for 2 hours
  4. customthe product precipitates
  5. filtrationThe product is filtered off
  6. washwashed thoroughly with water
  7. customdried under vacuum at 50° C

Sources & evidence

ORD record
ord-b89ec9fd3b274468a2d31c8ca03ea5fe
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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