Comparative assessment of an alternative route to (5-benzylfuran-3-yl)methanol (Elliott's alcohol), a key intermediate for the industrial production of resmethrins

Industrial preparation of resmethrin, one of the first members of the pyrethroid family to be introduced, is achieved via Elliott's alcohol. Available procedures make use of stoichiometric amounts of pyridine, thionyl chloride, fuming nitric acid and a lot of chlorinated by-products are generated. We present here an alternative route to Elliott's alcohol, based on Baylis-Hillman reaction in aqueous media. A comparative quantitative assessment of the "greenness" was performed, using the freeware package EATOS which takes into account both the mass economy and the environmental impact of the materials involved.