{{Chembox |verifiedrevid = 461114840 |ImageFile = Furoin.png |ImageSize = 100px |IUPACName = 1,2-bis(2-furyl)-2-hydroxy-ethanone |Section1={{Chembox Identifiers |CASNo = 552-86-3 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}}

| UNII = FP41RNB020 |ChEMBL_Ref = {{ebicite|correct|EBI}} |ChEMBL = 364893 |EINECS = 209-024-8 |PubChem = 11100 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 10629 |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = MIJRFWVFNKQQDK-UHFFFAOYSA-N |SMILES = O=C(c1occc1)C(O)c2occc2 |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 1S/C10H8O4/c11-9(7-3-1-5-13-7)10(12)8-4-2-6-14-8/h1-6,9,11H }} |Section2={{Chembox Properties | C=10 | H=8 | O=4 }} }}

'''Furoin''' or '''1,2-di(furan-2-yl)-2-hydroxyethanone''' is an organic compound with formula C<sub>10</sub>H<sub>8</sub>O<sub>4</sub>. It can be produced from furfural by a benzoin condensation reaction catalyzed by cyanide ions.<ref name=Lorient>Denis Lorient (1999), ''[https://books.google.com/books?id=EnPMWNp4-L0C&dq=furoin New ingredients in food processing: biochemistry and agriculture].'' Woodhead Publishing {{ISBN|1-85573-443-5}} 366 pages</ref>

==Reactions== Furoin synthesis from furfural is also catalyzed by vitamin B<sub>1</sub> (thiamine). In 1957, Ronald Breslow proposed that this reaction involves a relatively stable carbene form of thiamine.<ref>{{cite journal |title = Mechanism of Thiamine Action: Participation of a Thiazolium Zwitterion |author = Ronald Breslow |journal = Chemistry and Industry |volume = 26 |pages = 893 |year =1957}}</ref><ref>{{cite journal |title = Rapid Deuterium Exchange in Thiazolium Salts |author = R. Breslow |journal = Journal of the American Chemical Society |volume = 79 |issue = 7 |pages = 1762–1763|year = 1957 |doi = 10.1021/ja01564a064}}</ref> In the catalytic cycle shown below two molecules of furfural react to give furoin, via a thiazol-2-ylidene catalyst, resulting from loss of one proton at carbon 2 of the thiazolium cation of vitamin B<sub>1</sub>:

center|thumb|600px|Furoin formation from furfural, catalysed by thiamine

This was the first evidence for the existence of persistent carbenes.

==Uses== Furoin has been used as a plasticizer.<ref name=Lorient/>

==References== {{reflist}} Category:Acyloins Category:Plasticizers Category:2-Furyl compounds