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

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.