2,3-Dimethoxybenzoic acid → 2,3-Dihydroxybenzoic Acid

HRID 1453989Notes

Reaction equation

HRID 1453989 reaction equation
C[O:2][C:3]1[C:11]([O:12]C)=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].I>C(O)(=O)C.O>[OH:2][C:3]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 152042,3-Dimethoxybenzoic acidHCID 24841Hydrogen iodide

Product 1

HCID 192,3-Dihydroxybenzoic AcidYield 99.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2,3-Dimethoxybenzoic acid (2 g, 10.98 mmol) was dissolved in acetic acid (25 mL). Hydroiodic acid solution (25 mL, 47% in water) was added and the reaction stirred under reflux overnight. The reaction was allowed to cool to room temperature and the solvent removed in vacuo. The yellow solid obtained was dissolved in a minimum amount of water and extracted with EtOAc (4×50 mL). Organic layers were combined, washed with Na2S2O3 (10% solution, 2×50 mL), water (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield 1.68 g (99%) 2,3-dihydroxybenzoic acid as a white solid. 1H NMR (CD3OD): 7.34 (d, J =8.0 Hz, 1H), 6.99 (d, J=8.0 Hz, 1H), 6.72 (t, J=8.0 Hz, 1H).

Workup

  1. temperatureunder reflux overnight
  2. customthe solvent removed in vacuo
  3. customThe yellow solid obtained
  4. extractionextracted with EtOAc (4×50 mL)
  5. washwashed with Na2S2O3 (10% solution, 2×50 mL), water (50 mL) and brine (50 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a1d329e1a984f95bd8d622a9a027e47
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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