Comparative Studies on the Mechanochemistry of Guaiacylglycerol- and Veratrylglycerol- β -Guaiacyl Ether

Abstract Treatments of guaiacylglycerol- and veratrylglycerol-β-guaiacyl ether [I] and [II] with CBM, VBM and laboratory refiner furnished α-(2-methoxyphenoxy)-β-hydroxypropioguaiacone 1 as the major product in addition to a few small compounds 2-7 in relatively low yields. In addition, 5,5′-condensation reaction of compound [I] gave compounds 8 9, and 10. Alternatively, Cα-Cβ splitting reaction of veratrylglycerol-β-guaiacyl ether [II] occurrsby the mechanical treatment to give a number of products (6,11-14, and 15). Compounds [II] also formed p-carbonyl phenol 1 and products 2 4, and 7 by an alternate route. For comparison, mechanical treatments of vanillyT alcohol [III],α-methyl vanillyl alcohol [IV], and veratryl alcohol [V] were made with a ceramic ball mill (CBM), vibration ball mill (VBM), respectively. Former two gave vanillin 15 and acetovanillone 16, but no product was found from veratryl alcohol [V].