Hydrogen Peroxide → 4-Methanesulphinyl-3-nitrobenzoic acid

HRID 635400Notes

Reaction equation

HRID 635400 reaction equation
CSC1C=CC(C(O)=O)=CC=1[N+]([O-])=O.[CH3:15][S:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28])=[O:17].OO.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C>[CH3:15][S:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28])=[O:17]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 656671Sodium PyrosulfiteHCID 867564134-Methanesulphinyl-3-nitrobenzoic acid 4-Methylthio-3-nitrobenzoic acid

Product 1

HCID 221686484-Methanesulphinyl-3-nitrobenzoic acidYield 181.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The starting materials were prepared as follows: 4-Methanesulphinyl-3-nitrobenzoic acid 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 mN). 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 238-2390. Nmr (DMSO-d6): δ 2.90 (s, 3H); 8.29 (d, 1H); 8.56 (dd, 1H); 8.68 (d, 1H).

Workup

  1. customThe starting materials were prepared
  2. customevaporated
  3. customThe residue was purified by chromatography on silica
  4. washeluting with methanol

Sources & evidence

ORD record
ord-5410e222e9284c0ead1a5a73df0a1aec
Source dataset
uspto-grants-2001_02
Patent number
US06187804B1

Reaction notes

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