2,3-Dihydroxybutanedioic Acid → HCID 102020809, compound

HRID 1451212Notes

Reaction equation

HRID 1451212 reaction equation
C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.[C:11]([C@@:14]1([OH:25])[C:19](=[O:20])[O:18][C:16](=[O:17])[C@@:15]1([C:22](=[O:24])[CH3:23])[OH:21])(=[O:13])[CH3:12].C(O)(=O)C(C(C(O)=O)O)O.C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>>[C:11]([C@:14]1([OH:25])[C:19](=[O:20])[O:18][C:16](=[O:17])[C@:15]1([C:22](=[O:24])[CH3:23])[OH:21])(=[O:13])[CH3:12]

Participants

6

Reactant 5

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 439655D-Tartaric acidHCID 129631015HCID 129631015, compound

Product 1

HCID 102020809HCID 102020809, compound

Procedure

Diacetyl-L-tartaric anhydride is prepared from D-tartaric acid in the manner described in "DIACETYL-d-TARTARIC ANHYDRIDE (Tartaric anhydride, diacetate of d-)", Organic Synthesis, Collective Volume 4, 242-243 (1963). Briefly, a tartaric acid isomer or mixture of isomers is treated with acetic anhydride with a catalytic amount of sulfuric acid. The solution is heated gently for about 10 minutes and poured into an ice bath. The crystalline material formed is collected on a filter and is washed with toluene and ether and dried over phosphorus pentoxide and paraffin shavings. The crystalline bisacetyltartaric anhydride is used as is described in the following paragraph.

Workup

  1. temperatureThe solution is heated gently for about 10 minutes
  2. additionpoured into an ice bath
  3. customThe crystalline material formed
  4. customis collected on
  5. filtrationa filter
  6. washis washed with toluene and ether
  7. dry with materialdried over phosphorus pentoxide and paraffin shavings

Sources & evidence

ORD record
ord-7f25c643d0354ca38ccb81944882f0cf
Source dataset
uspto-grants-1997_02
Patent number
US05604220

Reaction notes

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