Selective Formation of 2-Hydroxy-3,3-bis(hydroxymethyl)-γ-butyrolactone from Formaldehyde on Hydrotalcite-Type Catalysts

Abstract

As a model for prebiotic sugar formation under neutral to acidic conditions, reactions of formaldehyde over hydrotalcite-type catalysts were investigated. Heating an aqueous solution of formaldehyde at 140—200 °C for 12 h over Ni–Fe hydrotalcite-type catalyst afforded 2-hydroxy-3,3-bis(hydroxymethyl)-γ-butyrolactone selectively, a 5.8% yield based on gas–liquid chromatographic analysis. The structure was identified by ¹H and ¹³C NMR and ¹H–¹³C HSQC, HMBC and ¹³C–¹³C 2D INADEQUATE NMR experiments.