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

HRID 1436686Notes

Reaction equation

HRID 1436686 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-].[Na+].Cl>CO>[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 14798Sodium HydroxideHCID 2758568Dimethyl 5-iodoisophthalate

Product 1

HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 5-iodo-isophthalic acid dimethyl ester (10 g, 31.2 mmol) in methanol (90 mL) and cool to 0° C. Add 2 N NaOH (15.6 mL) dropwise and slowly warm up to room temperature. Stir overnight and acidify to about pH=3 with 5 N HCl. Extract with ethyl acetate (2×50 mL). Wash the combined organic layers by water, saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound as a crude residue which is used in the next step without further purification.

Workup

  1. temperatureslowly warm up to room temperature
  2. extractionExtract with ethyl acetate (2×50 mL)
  3. washWash the combined organic layers by water, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-2fd71d46e3b54116b923465486d97028
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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