A New Route to Monhydroxycyrene

Majed Almuqhim; Con R. McElroy; Jiajun Fan

doi:10.53941/rc.2025.100003

Abstract

The importance of levoglucosenone (LGO) as a bio-derived platform molecule has been significantly elevated through its transformation into Cyrene™, a widely adopted green solvent. In this study, we investigate the interactions of LGO with water, a key component of biorefinery systems, revealing a new, efficient route to monohydroxycyrene (MHC). This transformation involves the slow, aqueous-based conversion of LGO to a triol intermediate, followed by selective dehydration to form MHC—a chiral molecule with dual functional groups and promising synthetic potential. MHC was synthesised in two simple and green steps without the need for catalysts or reagents, achieving an 88% yield and 98% purity under mild conditions. This environmentally benign approach aligns with the principles of green chemistry by eliminating the need for hazardous reagents and employing water as a sustainable solvent. The structure of MHC was confirmed using a combination of NMR, IR, UV-Vis, CHN, MS, and thermal analyses. Our results also highlight the role of temperature in influencing product formation, with lower temperatures (45–65 °C) enhancing yield, while higher temperatures (e.g., 95 °C) reduce conversion efficiency. MHC exhibits favourable physical and chemical properties, including polarity, solubility, and thermal stability, making it a promising candidate for future applications in green chemistry, pharmaceuticals, and materials science. The combined reactivity of the carbonyl and hydroxyl groups makes MHC a promissing platform molecule for synthesising polymers, pharmaceuticals, and advanced bio-based materials. Moreover, the mild reaction conditions and catalyst-free nature of the process contribute to reduced energy input and lower environmental impact. This work offers new insights into sustainable chemical pathways and provides a strong foundation for scaling up the production of novel biomass-derived building blocks.

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