2,3-Dihydroxybenzoic Acid → HCID 15730197, compound

HRID 2051163Notes

Reaction equation

HRID 2051163 reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[OH:6][C:7]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:17]O>>[CH3:17][O:10][C:9]([C:8]1[CH:12]=[C:13]([S:1]([OH:3])(=[O:5])=[O:2])[CH:14]=[C:15]([OH:16])[C:7]=1[OH:6])=[O:11]

Participants

4

Reactant 3

HCID 192,3-Dihydroxybenzoic AcidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 15730197HCID 15730197, compound

Procedure

Concentrated sulphuric acid (4 ml) and 2,3-dihydroxybenzoic acid (1 g) were heated at 60° C. for 1 hour. Methanol (15 ml) was added and the solution stirred under reflux for a further 3 hours. The solvent was evaporated and the residue purified on Diaion HP 20 SS resin (aqueous methanol with 1% acetic acid) to give 3-methoxycarbonyl-4,5-dihydroxybenzene sulphonic acid (1.8 g); δ(DMSO-d6); 3.88(s,3H); 7.32(d,1H); 7.57(d,1H). This was treated as in F (above) (chromatography on silica with methanol/dichloromethane as eluent) to give the title compound as a crystalline solid; δ(CDCl3); 1.31(s,6H); 1.38(s,6H); 2.80-3.20(m,2H); 3.92(s,3H); 8.04(d,1H); 8.50(d,1H).

Workup

  1. temperatureunder reflux for a further 3 hours
  2. customThe solvent was evaporated
  3. customthe residue purified on Diaion HP 20 SS resin (aqueous methanol with 1% acetic acid)

Sources & evidence

ORD record
ord-66b827453d784e41ae9473906cc4f6c8
Source dataset
uspto-grants-1991_05
Patent number
US05017569

Reaction notes

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