Hydrochloric Acid → 3-Hydroxy-4-iodobenzoic acid

HRID 2181647Notes

Reaction equation

HRID 2181647 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[I:11]I.Cl>[NH4+].[OH-].O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 807IodineHCID 74203-Hydroxybenzoic Acid

Product 1

HCID 7368543-Hydroxy-4-iodobenzoic acidYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

3-Hydroxybenzoic acid (13.8 g, 100 mmol) is dissolved in concentrated NH4OH (200 mL) using an overhead stirrer and is treated slowly drop-wise with a solution of iodine (23.4 g, 92 mmol) and KI (18.26 g, 110 mmol) in water (100 mL). The solution is stirred for 1 h at RT and then treated rapidly drop-wise with concentrated HCl (180 mL). The solid is collected via filtration, rinsed with water and dried overnight by pulling air through the solid to afford 13.1 g (54%) of 3-hydroxy-4-iodobenzoic acid as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 7.13, 7.43, 7.80, 10.71, 12.98 ppm.

Workup

  1. additiontreated rapidly
  2. filtrationThe solid is collected via filtration
  3. washrinsed with water
  4. customdried overnight

Sources & evidence

ORD record
ord-e0e6e15c54654baab9972818db0eae9a
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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