Water → 3-Iodo-4-methylbenzoic acid

HRID 2068412Notes

Reaction equation

HRID 2068412 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-4e0b962c5560471882cd366d5064c1a8
Source dataset
uspto-grants-2012_10
Patent number
US08293909B2

Reaction notes

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