Comparative Studies on the Mechanochemistry of Guaiacylglycerol- and Veratrylglycerol- β -Guaiacyl Ether
Titel:
Comparative Studies on the Mechanochemistry of Guaiacylglycerol- and Veratrylglycerol- β -Guaiacyl Ether
Auteur:
Itoh, Kazutaka Sumimoto, Masashi Tanaka, Hiroo
Verschenen in:
Journal of wood chemistry and technology
Paginering:
Jaargang 15 (1995) nr. 3 pagina's 395-411
Jaar:
1995-08-01
Inhoud:
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 89, 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 24, 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].