2,3-Dihydroxybenzoic Acid → HCID 15730195, compound

HRID 2051162Notes

Reaction equation

HRID 2051162 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].ClCCl>CCOCC>[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])([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 192,3-Dihydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 6344Dichloromethane

Product 1

HCID 15730195HCID 15730195, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Concentrated sulphuric acid (1 ml) and 2,3-dihydroxybenzoic acid (0.5 g) were heated at 60° C. for 1 hour. The mixture was cooled, taken up in ether (20 ml), poured into dichloromethane (200 ml) and cooled to give as crystals, 3-carboxy-4,5-dihydroxybenzenesulphonic acid (0.31 g); δ(DMSO-d6); 7.34(d,1H); 7.61(d,1H). To a suspension of this acid (1 g) in acetonitrile (10 ml) was added triethylamine (2.4 ml), followed by isobutyryl chloride (1.5 ml). The solution was stirred at room temperature for 1 hour, the solvent was evaporated and the residue purified by chromatography on Diaion HP 20 SS resin (aqueous methanol containing 1% acetic acid) to give 3-carboxy-4,5-di-isobutyroxybenzene sulphonic acid (1.2 g); δ(DMSO-d6): 1.19(s,6H); 1.27(s,6H); 2.90-3.15(m,2H); 7.63(d,1H); 8.04(d,1H).

Workup

  1. temperatureThe mixture was cooled
  2. temperaturecooled

Sources & evidence

ORD record
ord-388451ec506b4011870e75e43e7de8c1
Source dataset
uspto-grants-1991_05
Patent number
US05017569

Reaction notes

Loading…