Water → 3-Iodo-4-methylbenzoic acid

HRID 219415

Reaction equation

HRID 219415 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([I:11])[CH:5]=1.[OH-].[Na+].O>CO>[I:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH3:10])[C:3]([OH:12])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13614033Methyl 3-iodo-4-methylbenzoate

Product 1

HCID 6216403-Iodo-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-3-Iodo-4-methylbenzoate (3 g, 109 mmol, 1 eq) dissolved in MeOH (30 ml) was added sodium hydroxide (1.3 g, 327 mmol, 3 eq) followed by the addition of water (15 ml). The above solution was stirred at room temperature for 14 h. The solution was concentrated under vacuum, and then added water. The pH of the reaction was bought to 3 using Conc. HCl. The solid obtained was filtered and dried under vacuum. Yield: 2.7 g (96%). 1HNMR (400 MHz, DMSO-d6): δ 2.44 (s, 3H), 7.45 (d, J=8.00 Hz, 1H), 7.85 (d, J=3.18 Hz, 1H), 8.31 (s, 1H).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customThe solid obtained
  3. filtrationwas filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c800058eea974e828f5dd433dd8e29d4
Source dataset
uspto-grants-2012_06
Patent number
US08198449B2

Linked notes

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