Water → Methyl 3-hydroxy-4-iodobenzoate

HRID 390624Notes

Reaction equation

HRID 390624 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 377.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Overall, 61.31 g of 3-hydroxy-4-iodobenzoic acid are obtained in the form of a white solid. 47 g (150 mmol) of this 3-hydroxy-4-iodobenzoic acid are placed in 300 mL of methanol and 6.13 g (35.6 mmol) of para-toluenesulfonic acid are added. The reaction mixture is heated at 70° C. for 48 hours.— The reaction is stopped by addition of 11 of water. The precipitated product is filtered off and rinsed with water to neutral pH. 37.4 g (76%) of methyl 3-hydroxy-4-iodobenzoate are obtained in the form of a beige-colored powder.

Workup

  1. filtrationThe precipitated product is filtered off
  2. washrinsed with water to neutral pH

Sources & evidence

ORD record
ord-0a2fc284b386424b986288fa609a2cbf
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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