Malic Acid → 2,5-Dioxooxolan-3-yl acetate

HRID 1462605Notes

Reaction equation

HRID 1462605 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=O)[OH:3].S(=O)(=O)(O)O.[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[C:15]([O:3][CH:2]1[CH2:4][C:5](=[O:7])[O:8][C:1]1=[O:9])(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 525Malic AcidHCID 1118Sulfuric AcidHCID 7918Acetic Anhydride

Product 1

HCID 5394912,5-Dioxooxolan-3-yl acetateYield 60%

Conditions

Temperature
140 °C

Procedure

250 g (1.86 mole) of malic acid are dissolved in 500 ml of acetic anhydride and a further 1 ml of concentrated sulphuric acid is added thereto. The mixture is then heated at 140° C. for four hours. Finally, it is concentrated in vacuo and the residue is fractionally distilled. 2-acetoxysuccinic acid anhydride is obtained in a 60% yield. Boiling point at 0.01 torr: 108° to 113° C.; melting point: 56° C.

Workup

  1. concentrationFinally, it is concentrated in vacuo
  2. distillationthe residue is fractionally distilled

Sources & evidence

ORD record
ord-39a962399bec4bc39c598bc855ffb970
Source dataset
uspto-grants-1984_07
Patent number
US04460782

Reaction notes

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