Sodium Iodide → 3-Hydroxy-4-iodobenzoic acid

HRID 858275Notes

Reaction equation

HRID 858275 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].[I-:13].[Na+].Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:13])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 74203-Hydroxybenzoic AcidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 23665760Sodium Hypochlorite

Product 1

HCID 7368543-Hydroxy-4-iodobenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

25.00 g (180.0 mmol) of 3-hydroxybenzoic acid, 7.20 g (180.0 mmol) of sodium hydroxide pellets, 27.13 g (180.0 mmol) of sodium iodide and 500 ml of methanol are introduced into a one-litre three-necked flask under a stream of nitrogen. The mixture is cooled to 0° C. and 374.30 g (180.0 mmol) of an aqueous sodium hypochlorite solution are added dropwise over one hour and fifty minutes. The reaction medium is stirred for two hours at 0° C., a sodium thiosulphate solution is then added, the mixture is acidified at pH 5, extracted with ethyl ether, the organic phase is washed with water to neutral pH, dried over magnesium sulphate and filtered and the solvents are evaporated off. 43.80 g (92%) of the expected compound are collected in the form of a beige-coloured powder with a melting point of 198° C.

Workup

  1. extractionextracted with ethyl ether
  2. washthe organic phase is washed with water to neutral pH
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvents are evaporated off
  6. custom43.80 g (92%) of the expected compound are collected in the form of a beige-coloured powder with a melting point of 198° C.

Sources & evidence

ORD record
ord-adbafa63eddf4547b5d65c98ade37c58
Source dataset
uspto-grants-2006_12
Patent number
US07148245B2

Reaction notes

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