Two-Dimensional ITQ-2 Zeolite for Biomass Transformation: Synthesis of Alkyl 5-Benzyl-2-furoates as Intermediates for Fine Chemicals

A new catalytic process to produce alkyl 5-benzyl-2-furoates has been performed through a two-step process that involves (a) selective oxidative esterification of 5-hydroxymethylfurfural (HMF) to 5-hydroxymethyl furoic acid methyl ester (HMFE) using Au/TiO2 as catalyst and oxygen as oxidant and (b) alkylation of benzene derivatives with HMFE using zeolites as acid catalysts. The alkylation process has been carried out using large pore tridimensional zeolites such as Beta and USY, a mesoporous aluminosilicate (MCM-41), and a two-dimensional delaminated ITQ-2 zeolite. The results showed that ITQ-2 zeolite, which combines easy product diffusion and adequate acitidy, was the most active and selective catalyst to produce alkyl 5-benzyl-2-furoates. Finally, we have presented a simple protocol to prepare 5-(4-fluorobenzyl)-2-furyl methyl ketone, a key intermediate in the synthesis of S-1360, an antiviral for the treatment of AIDS, in good yield through a more sustainable method than the existing ones, starting from biomass platform molecules.