Two dimensional ITQ-2 zeolite for biomass transformation: Synthesis of alkyl 5-benzyl-2-furoates as intermediates for fine chemicals

[EN] A new catalytic process to produce alkyl 5-benzyl-2-furoates has been performed through 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 2D delaminated ITQ-2 zeolite. The results showed that ITQ-2 zeolite which combines an 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 that the existing ones, starting from biomass platform molecules.
Spanish MICINN Project CTQ:2015-67592-P, Generalitat Valenciana (Prometeo program) and Program Severo Ochoa are gratefully acknowledged.