71653-33-3Relevant academic research and scientific papers
Synthesis of Urushiol Derivatives by the Fries Rearrangement
Jefferson, Alan,Wangchareontrakul, Sirichai
, p. 605 - 614 (2007/10/02)
The photo- and thermal-induced Fries rearrangement reactions of some unsaturated aliphatic esters of benzene-1,2-diol (catechol) have been studied.Photorearrangement and thermal rearrangement favoured products correspond to ortho and para migration respectively, but the thermal rearrangement may be acompanied by indanones, chromanones and other products which were formed through subsequent side reactions of the double bond.Photoinduced Fries rearrangement of 2-hydroxyphenyl oleate followed by reduction of the carbonyl group gave monosubstituted catechol derivatives with an unsaturated C18 side chain in either the 3- or 4-position.These alkenylcatechol derivatives are related in structure to chemical components isolated from oriental lacquer trees, such as urushiol from Rhus verniciflua or thitsiol from Melanorrhoea usitata
