Acetic Anhydride → Tetrahydro-2,5-dioxo-3-furansulfonic Acid, Sodium Salt

HRID 443056Notes

Reaction equation

HRID 443056 reaction equation
[S:1]([CH:5]([CH2:9][C:10]([OH:12])=[O:11])[C:6]([OH:8])=O)([OH:4])(=[O:3])=[O:2].[OH-].[Na+:14].C(OC(=O)C)(=O)C>C(OCC)(=O)C>[Na+:14].[O:8]=[C:6]1[CH:5]([S:1]([O-:4])(=[O:3])=[O:2])[CH2:9][C:10](=[O:11])[O:12]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 21220Sulfosuccinic acid monosodium salt

Product 1

HCID 4187165Tetrahydro-2,5-dioxo-3-furansulfonic Acid, Sodium Salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tetrahydro-2,5-dioxo-3-furansulfonic acid sodium salt was prepared by stirring 1.71 moles of sulfosuccinic acid with 1.87 moles of sodium hydroxide at 50° C. until a milky suspension formed and then adding 1 kg acetic anhydride over 6 hours. After cooling, 1 L of ethyl acetate was added and the mixture was filtered. The filter cake was washed with 500 mL ethyl acetate. On drying 344.32 g of white crystalline product was obtained. 13C-NMR (d6-DMSO) 171.3, 167.2, 60.4, 34.0 ppm.

Workup

  1. customformed
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washThe filter cake was washed with 500 mL ethyl acetate
  5. dry with materialOn drying 344.32 g of white crystalline product
  6. customwas obtained

Sources & evidence

ORD record
ord-6de906056f5747b189ab98023485bc0a
Source dataset
uspto-grants-1999_04
Patent number
US05892057

Reaction notes

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