Elsevier, Tetrahedron, 25(65), p. 4866-4870, 2009
DOI: 10.1016/j.tet.2009.04.042
Wiley-VCH Verlag, ChemInform, 39(40), 2009
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Allyl esters can be obtained by a Finkelstein-rearrangement–elimination reaction of 2-chloro-1-(chloromethyl)ethyl esters induced by NaI. Sodium iodide can be used below equivalence using a reductive agent as sodium thiosulfate. High yields are obtained with most of the diverse esters studied. The method described avoids the use of allyl alcohol as a reagent. 2-Chloro-1-(chloromethyl)ethyl esters are prepared from glycerol, the main by-product of biodiesel industry. The effectiveness of iodine as reagent to hydrolyze allyl esters is also confirmed. ; This work was supported in part by a Grant-in-Aid for the Secretaría de Estado de Política Científica y Tecnológica of the Spanish Ministry of Education and Culture (Contract grant number: CTQ2006-07451/PPQ). The authors are grateful to the Comissionat per a Universitats i Recerca del Departament d'Innovació, Universitats i Empresa de la Generalitat de Catalunya and to the European Social Fund (ESF) for the FI grant of Marc Escribà Gelonch.