SELECTIVE HYDROXYMETHYLATION OF GUAIACOL IN THE PRESENCE OF BETA-CYCLODEXTRIN

Studies on the effect of beta-cyclodextrin (BCD) and its derivatives o n the selectivity in hydroxymethylation of guaiacol by formaldehyde wa s carried out. Fairly high selectivity with respect to isovanillyl alc ohol formation was achieved. Significantly, the selectivity-enhancing effects of 2,6-di-O-methyl-BCD was much larger, giving rise to 22% mor e of isovanillyl alcohol formation than BCD and its polymer. UV, fluor escence, H-1-NMR spectroscopic and potentiometric studies were also ca rried out to determine the orientation of guaiacol inside the BCD cavi ty.