Hydrogen Peroxide → 4-Methanesulphinyl-3-nitrobenzoic acid

HRID 341886Notes

Reaction equation

HRID 341886 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].OO.S(S([O-])=O)([O-])(=O)=[O:18].[Na+].[Na+]>C(O)(=O)C>[CH3:1][S:2]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])=[O:18]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 5425314-Methylthio-3-nitrobenzoic acidHCID 656671Sodium Pyrosulfite

Product 1

HCID 221686484-Methanesulphinyl-3-nitrobenzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methylthio-3-nitrobenzoic acid (4.36 g, 20 mM) was dissolved in acetic acid (200 ml), and treated at ambient temperature with H2O2 (2.5 ml, 30%, 22 mM). After stirring at ambient temperature for 4 days, excess peroxide was decomposed with sodium metabisulfite, and solvent evaporated. The residue was purified by chromatography on silica, eluting with methanol, to give 4-methanesulphinyl-3-nitrobenzoic acid (4.1 g, 89%), mp 238°-239°. Nmr (DMSO-d6): δ 2.90 (s, 3H); 8.29 (d, 1H); 8.56 (dd, 1H); 8.68 (d, 1H).

Workup

  1. customevaporated
  2. customThe residue was purified by chromatography on silica
  3. washeluting with methanol

Sources & evidence

ORD record
ord-044f1f81902f4c72bb05b100d62ef2a7
Source dataset
uspto-grants-1999_01
Patent number
US05856321

Reaction notes

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