Water → 3-Hydroxy-4-iodobenzoic acid

HRID 1951970Notes

Reaction equation

HRID 1951970 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].O>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 962WaterHCID 5238Sodium IodideHCID 74203-Hydroxybenzoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 7368543-Hydroxy-4-iodobenzoic acidYield 31.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

21 g (520 mmol) of sodium hydroxide and then 79 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 then Javel water (520 mmol) is added dropwise. The reaction mixture is stirred at 0-5° C. for 2 hours and then at room temperature for 15 h. After evaporating the methanol, the reaction mixture is acidified with a concentrated solution of hydrochloric acid. The precipitate is filtered, washed with water and dried. 41.9 g of 3-hydroxy-4-iodobenzoic acid is obtained in the form of a white solid with melting point of 218° C. The aqueous phase is extracted with ethyl acetate, the organic phase obtained is dried over magnesium sulfate, filtered, and evaporated. The residue obtained is taken up in heptane and the precipitate obtained is filtered.

Workup

  1. waitat room temperature for 15 h
  2. customAfter evaporating the methanol
  3. filtrationThe precipitate is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-653ddc8363bc4ea69e2b81f42f3108b8
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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