Hemicellulose from biomass comprises mostly of xylose, an aldopentose which can be readily hydrolyzed and dehydrated to furfural. Identifying value added organic products derived from biomass is an important goal for achieving sustainable materials production. In this work, potentially polymerizable 5,5'-(propane-2,2-diyl)bis(furan-5,2-diyl)dimethanol has been synthesized in 4-steps from furfural. Commercially available furfural was reacted with 1,2-ethanedithiol in recyclable glycerol produced the 1,3-dithiane protected furfural in 69% yield after distillation. The intermediate on treatment with acetone and 50% aqueous sulfuric acid produced a dimerized Friedel Crafts product in 58% yield. Deprotection of the 1,3-dithiane accomplished with selenium dioxide-acetic acid to generate dialdehyde in 90% yield. The dialdehyde was reduced to afford the final diol in 96 % yield. The stable, colorless, and crystalline target was characterized by standard methods as well as by x-ray crystallography.

Synthesis of 5,5'-(propane-2,2-diyl)bis(furan-5,2-diyl)dimethanol from biomass

244th National Meeting (2012)

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