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Dioxalin

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Dioxalin
Names
IUPAC name 5-(Hydroxymethyl)-1,4-dioxane-2,3-dione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H6O5/c6-1-3-2-9-4(7)5(8)10-3/h3,6H,1-2H2Key: LLQXEQGCIRCAQO-UHFFFAOYSA-N
SMILES
  • OCC1COC(=O)C(=O)O1
Properties
Chemical formula C5H6O5
Molar mass 146.098 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dioxalin is a reaction product of glycerol with oxalic acid at 533 K. Its IUPAC name is 5-(hydroxymethyl)-1,4-dioxane-2,3-dione. Dioxalin readily loses two molecules of carbon dioxide at this high temperature to form allyl alcohol and therefore offers a method for conversion of glycerol to allyl alcohol.

References

  1. Chattaway, Frederick Daniel (1915). "XLVII.—The preparation of allyl alcohol". J. Chem. Soc., Trans. 107: 407–410. doi:10.1039/CT9150700407.
  2. Coffey, Samuel; Ward, Charles Frederick (1921). "CXLVIII.—The preparation of some allyl compounds". J. Chem. Soc., Trans. 119: 1301–1306. doi:10.1039/CT9211901301.
  3. Arora, Amit (2006). Carbohydrates and Proteins. Discovery Publishing House. p. 48. ISBN 978-81-8356-178-5.
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