Article Dans Une Revue ACS Sustainable Chemistry & Engineering Année : 2019

Proline-mediated Knoevenagel condensation in ethanol: a sustainable access to p-hydroxycinnamic acids

Résumé

Naturally occurring p-hydroxycinnamic acids were obtained using an amine-and toxic solvent-free Knoevenagel-type pathway. This method uses not only non-toxic reagents (i.e., L-proline and magnesium oxide as catalyst) and ethanol as green solvent, all reagents and solvent being renewable and accessible at low price. By combinaing a Design of Experiment and a One Variobale At a Time optimization (OVAT), the different reaction parameters optimized in order to favor sinapic acid synthesis over that of the two other possible by-products, the corresponding di-acids and vinyl phenols. This alternative to classical Knoevenagel reaction allowed to substitute traditional pyridine-and piperidine-catalyzed pathway while obtaining each natural p-hydroxycinnamic acids in good conversions and yields (50-85%).

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hal-02883331 , version 1 (29-06-2020)

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Cedric Peyrot, Aurélien Peru, Louis Mouterde, Florent Allais. Proline-mediated Knoevenagel condensation in ethanol: a sustainable access to p-hydroxycinnamic acids. ACS Sustainable Chemistry & Engineering, 2019, 7 (10), pp.9422-9427. ⟨10.1021/acssuschemeng.9b00624⟩. ⟨hal-02883331⟩
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