4-Hydroxybenzoic Acid → 4-Hydroxy-3-iodobenzoic acid (2IPCOOH)

HRID 710401Notes

Reaction equation

HRID 710401 reaction equation
[I:1]I.[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1>O.[NH4+].[OH-]>[I:1][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[OH:3])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 807Iodine

Product 1

HCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)Yield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A solution of I2 (1.06 g; 4.18 mmol) and KI (3.41 g; 20.54 mmol) in H2O was added at once to a solution of 4-hydroxybenzoic acid (0.58 g; 4.18 mmol) in 25% NH4OH (22 ml). The reaction mixture turn instantly from black to colourless upon stirring at room temperature. This was evaporated under reduced pressure, diluted to 5 ml with H2O and acidified to pH˜5 with 10% citric acid. The solid formed was filtered off, washed with H2O (2×5 ml) and dried to give title compound (0.91 g; 89%), as colourless solid. 1H-NMR (DMSO-d6) 6.9 (d, 1H, J=8.5 Hz); 7.75 (dd, 1H, J=2, 8.5 Hz); 8.17 (d, 1H, J=2 Hz); 11.4 (s, 1H).

Workup

  1. customThis was evaporated under reduced pressure
  2. additiondiluted to 5 ml with H2O
  3. customThe solid formed
  4. filtrationwas filtered off
  5. washwashed with H2O (2×5 ml)
  6. customdried

Sources & evidence

ORD record
ord-26a1b33bd29a4b53a8838abb2780e2c6
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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