Water → Methyl 3-hydroxy-4-iodobenzoate

HRID 1951971Notes

Reaction equation

HRID 1951971 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[I:22])[C:16]([OH:18])=[O:17].O>CO>[OH:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[I:22])[C:16]([O:18][CH3:1])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7368543-Hydroxy-4-iodobenzoic acid

Product 1

HCID 10378812Methyl 3-hydroxy-4-iodobenzoateYield 377.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

6.1 g (35.6 mmol) of paratoluene sulfonic acid is added to a solution of 47 g (150 mmol) of 3-hydroxy-4-iodobenzoic acid in 300 ml of methanol. The reaction mixture is heated at 70° C. for 48 hours. After adding 1000 ml of water, the precipitate is filtered, and rinsed with water to neutral pH. 37.4 g (76%) of methyl 3-hydroxy-4-iodobenzoate is obtained in the form of a beige powder.

Workup

  1. filtrationthe precipitate is filtered
  2. washrinsed with water to neutral pH

Sources & evidence

ORD record
ord-ed64a13087a841e3b8b6ecf9cafb8839
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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