2,3-Dihydroxybenzoic Acid → HCID 178524661, compound

HRID 1461874Notes

Reaction equation

HRID 1461874 reaction equation
[OH:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[K+:13].[S:14](=[O:18])(=[O:17])([OH:16])[OH:15]>O>[K+:13].[K+:13].[OH:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[OH:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([S:14]([OH:16])(=[O:18])=[O:15])=[CH:7][C:3]=1[C:4]([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 192,3-Dihydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 14797Potassium Hydroxide

Product 1

HCID 178524661HCID 178524661, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

2,3-Dihydroxybenzoic acid (15.4g, 0.1 moles) was dissolved in small portions at 5° C. in 80 ml of sulfuric acid containing 30% sulfur trioxide. The mixture was allowed to warm to 20° C. over 1 h and was then poured slowly into 1L of vigorously stirred ice water. The pH was adjusted to 4.5 with 30% potassium hydroxide and the solid formed was removed by filtration. The filtrate was diluted with a 1.5 fold volume of methanol and filtered again. This filtrate was evaporated to 200 ml and the pH was adjusted to 6.0 with potassium hydroxide. Acetone (500 ml) was added and the resulting white precipitate was filtered and dried to give 18 g of crude product. Chromatography of this solid on HP20 in water gave 12.8 g of pure title compound after lyophilization.

Workup

  1. customthe solid formed
  2. customwas removed by filtration
  3. additionThe filtrate was diluted with a 1.5 fold volume of methanol
  4. filtrationfiltered again
  5. customThis filtrate was evaporated to 200 ml
  6. additionAcetone (500 ml) was added
  7. filtrationthe resulting white precipitate was filtered
  8. customdried
  9. customto give 18 g of crude product

Sources & evidence

ORD record
ord-a3c7e14f301a44bca1768e99140853b3
Source dataset
uspto-grants-1991_12
Patent number
US05077432

Reaction notes

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