Dendrimers are the subject of intense attention recently because of their anticipated potentialities and the peculiar structural properties.A novel synthetic route for the preparation of functionalized dendrons built on the 1,3,5-benzenetricarboxaldehyde core and endowed with a periphery of pentaerythritol groups has been developed.1,3,5-Tri(2,6-dioxa-4,4-dihydroxymethyl cyclohexyl) benzene(1) was synthesized by the condensation of 1,3,5-benzenetricarboxaldehyde with pentaerythritol in the presence of hot CHCl3 and p-methyl benzene sulfonic acid with 55% yield.By turning 1,3,5-benzenetricarboxaldehyde into its trioxime,it was protected to decrease the cross-linked reaction with compound 1 both including many groups.The reaction of compound 1 with 1,3,5-benzenetricarboxaldehyde trioxime and pentaerythritol afforded 1,3,5-tri{3-[2,4,8,10 -tetra-oxa-9(3,5-di(2,6-dioxa-4,4-dihydroxymethylcyclohexyl) phenyl]spiro\undecyl}benzene(2) by using I2 as the catalyst,and the yield was 25.2%.Product 2 and its intermediates were identified by IR,1H NMR,MS spectra and elemental analysis.