Acetic Anhydride → Tetrahydro-2,5-dioxo-4-methyl-3-furansulfonic acid sodium salt

HRID 443058Notes

Reaction equation

HRID 443058 reaction equation
[Na+:1].[CH3:2][CH:3]([C:12]([O-:14])=[O:13])[CH:4]([S:8]([OH:11])(=[O:10])=[O:9])[C:5]([O-:7])=O.[Na+].C(OC(=O)C)(=O)C>>[Na+:1].[O:7]=[C:5]1[CH:4]([S:8]([O-:11])(=[O:10])=[O:9])[CH:3]([CH3:2])[C:12](=[O:13])[O:14]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1317212183-Methyl-2-sulfosuccinic acid sodium salt

Product 1

HCID 88081204Tetrahydro-2,5-dioxo-4-methyl-3-furansulfonic acid sodium saltYield 47.4%

Procedure

40 g 3-methyl-2-sulfosuccinic acid sodium salt (cis and trans diastereomers) was stirred with 50 g acetic anhydride and then heated to 86 degrees Centigrade while distilling over acetic acid for 1.5 hours. 100 mL ethyl acetate was added and the mixture was filtered. The precipitate was washed with 100 mL ethyl acetate. The precipitate was dried to produce 16.0 g yellowish-white solid. 1H-NMR (d6-DMSO) 3.40 ppm d J=10.52 Hz, 2.92-2.98 ppm m, 1.28-1.31 ppm m J=7.12 Hz.

Workup

  1. temperatureheated to 86 degrees Centigrade
  2. distillationwhile distilling over acetic acid for 1.5 hours
  3. addition100 mL ethyl acetate was added
  4. filtrationthe mixture was filtered
  5. washThe precipitate was washed with 100 mL ethyl acetate
  6. customThe precipitate was dried

Sources & evidence

ORD record
ord-faecedf0ad59473c85f286da8c0caf26
Source dataset
uspto-grants-1999_04
Patent number
US05892057

Reaction notes

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