Water → 4-Iodo-3-methoxybenzoic acid

HRID 471820Notes

Reaction equation

HRID 471820 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[OH-].[Na+].O>CO>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11243290Methyl 4-iodo-3-methoxybenzoate

Product 1

HCID 179342274-Iodo-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 4-iodo-3-(methyloxy)benzoate (3.25 g, 0.011 mol), sodium hydroxide (0.48 g, 0.012 mol) and water (30 mL) in methanol (30 mL) was heated in an oil bath at 65° C. for 3 hr. The mixture was concentrated in vacuo to remove the methanol and the aqueous residue was chilled in an ice bath. Concentrated aqueous hydrogen chloride was added until the pH was acidic and the mixture was stirred at ice bath temperature. The resulting solid was filtered, washed with water and dried to give 4-iodo-3-(methyloxy)benzoic acid as a white solid, used without further purification. LC/MS (method A) tR 2.35 min; m/z 279 (M+H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove the methanol
  3. temperaturethe aqueous residue was chilled in an ice bath
  4. additionConcentrated aqueous hydrogen chloride was added until the pH
  5. filtrationThe resulting solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-7bc9f6b1d6e64a91be4cd3d5b52c5c73
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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