Water → Methyl 3-hydroxy-4-iodobenzoate

HRID 1361089Notes

Reaction equation

HRID 1361089 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([O:7][CH3:12])=[O:6]

Participants

5

Reactant 3

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

Product 1

HCID 10378812Methyl 3-hydroxy-4-iodobenzoateYield 447.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 140 g (530 mmol) of 3-hydroxy-4-iodobenzoic acid and 20.2 g (110 mmol) of para-toluenesulfonic acid in 900 ml of methanol is refluxed for 18 hours. After cooling, 700 ml of water are added and the medium is stirred for 18 hours. The product precipitates and is filtered off. After drying under vacuum at 50° C., 137 g (93%) of methyl 3-hydroxy-4-iodobenzoate are obtained in the form of a white solid.

Workup

  1. temperatureAfter cooling
  2. customThe product precipitates
  3. filtrationis filtered off
  4. customAfter drying under vacuum at 50° C.

Sources & evidence

ORD record
ord-d5b74c15b02d4c3a825a103be0e7d6a0
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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