4-Hydroxy-3-iodobenzoic acid (2IPCOOH) → Methyl 4-hydroxy-3-iodobenzoate

HRID 2181652Notes

Reaction equation

HRID 2181652 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[I:11].Cl.[CH3:13]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[CH:4][C:3]=1[I:11]

Participants

3

Reactant 2

HCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)HCID 21893726Hydrochloride methanol

Product 1

HCID 11346465Methyl 4-hydroxy-3-iodobenzoateYield 36.3%

Conditions

Temperature
65 °C

Procedure

4-Hydroxy-3-iodobenzoic acid (59.6 g, 226 mmol) is combined with 3N HCl/MeOH (276 mL, 678 mmol) and heated to 65° C. for 24 h, then concentrated to dryness. The residue is diluted with water, neutralized to pH 7 with 3N NaOH and the resulting solid collected via filtration. The crude material is adsorbed onto silica gel and chromatographed over 1 kg of silica gel with 50% EtOAc/hexane. Fractions containing product are combined and concentrated to a solid (47.2 g). The material is recrystallized from EtOAc to afford 22.8 g (36%) of methyl 4-hydroxy-3-iodobenzoate as a white solid. HRMS (FAB) calcd for C8H7IO3+H: 278.9520, found 278.9534 (M+H)+.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue is diluted with water
  3. filtrationthe resulting solid collected via filtration
  4. customchromatographed over 1 kg of silica gel with 50% EtOAc/hexane
  5. additionFractions containing product
  6. concentrationconcentrated to a solid (47.2 g)
  7. customThe material is recrystallized from EtOAc

Sources & evidence

ORD record
ord-cb6f7c0fd292404f86211033b92617a4
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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