:Dioxalin
{{Chembox
| ImageFile = Dioxalin.svg
| ImageSize = 150px
| IUPACName = 5-(Hydroxymethyl)-1,4-dioxane-2,3-dione
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| Section1 = {{Chembox Identifiers
| CASNo =
| ChemSpiderID = 129557678
| PubChem = 139033612
| StdInChI=1S/C5H6O5/c6-1-3-2-9-4(7)5(8)10-3/h3,6H,1-2H2
| StdInChIKey = LLQXEQGCIRCAQO-UHFFFAOYSA-N
| SMILES = OCC1COC(=O)C(=O)O1
}}
| Section2 = {{Chembox Properties
| C = 5 | H = 6 | O = 5
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| Section3 = {{Chembox Hazards
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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.{{Cite journal | doi = 10.1039/CT9150700407 | title = XLVII.—The preparation of allyl alcohol | journal = J. Chem. Soc., Trans. | volume = 107 | pages = 407–410 | year = 1915 | last1 = Chattaway | first1 = Frederick Daniel | url = https://zenodo.org/record/2475515 }}{{cite journal |last1=Coffey |first1=Samuel |last2=Ward |first2=Charles Frederick |title=CXLVIII.—The preparation of some allyl compounds |journal=J. Chem. Soc., Trans. |date=1921 |volume=119 |pages=1301–1306 |doi=10.1039/CT9211901301|url=https://zenodo.org/record/1670183 }}{{cite book |last1=Arora |first1=Amit |title=Carbohydrates and Proteins |year=2006 |publisher=Discovery Publishing House |isbn=978-81-8356-178-5 |page=48 |url=https://books.google.com/books?id=9bSz1ZkJ41AC&pg=PA48 |language=en}}