Hydrochloric Acid → 3-Iodo-5-(methoxycarbonyl)benzoic acid

HRID 2388995Notes

Reaction equation

HRID 2388995 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([I:14])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Li+].Cl>CO.CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([I:14])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 2758568Dimethyl 5-iodoisophthalate

Product 1

HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acidYield 721.6%

Reagents, catalysts & solvents 1

HCID 21894497Aceton-methanolSolvent

Procedure

To a mixture of 5-Iodo-isophthalic acid dimethyl ester (9.00 g, 3.12 mmol) in methanol/acetone (3:1, 18 ml) was added 4 N aqueous lithium hydroxide (0.78 ml, 3.12 mmol). This mixture was stirred for 16 hours, neutralized with 1 N hydrochloric acid, extracted with ethyl acetate, dried over magnesium Sulfate and the solvent removed under reduced pressure. The crude was purified by silica gel chromatography to afford 5-iodo-isophthalic acid monomethyl ester (6.89 g, 80% yield) as a white solid. MS: m/z 306.1 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium Sulfate
  3. customthe solvent removed under reduced pressure
  4. customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3d6af2198161460480fdc7797c113003
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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