Synthesis of a new polymer-supported 1,3-diol and its application as a protecting group in solid-phase organic synthesis

✍ Scribed by Qi-Sheng Ren; Wen-Qiang Huang; Ping-Lum Ho

• Publisher: Elsevier Science
• Year: 1989
• Weight: 548 KB
• Volume: 11
• Category: Article
• ISSN: 0923-1137
• DOI: 10.1016/0923-1137(89)90109-7

✦ Synopsis

A new 1,3-diol-containing polymer, 1-polystyryl-2,2-dimethyl-l,3-propanediol (V1), has been prepared by aldol condensation and disproportionation of an isobutyrylated divinylbenzene (2 %)-styrene copolymer with paraformaldehyde in the presence of potassium hydroxide under anhydrous conditions. Polymer VI was used as a protecting group for one of the aldehydic functions of terephthalaldehyde through the acetal linkage. The unbound aldehydic groups on the polymer were then reacted in the solid phase with hydroxylamine, sodium borohydride, a Wittig reagent or a Grignard reagent, giving the corresponding polymer-anchored oximines, primary alcohols, olefins or secondary alcohols, respectively. Cleavage of the aeetal links with formic acid in chloroform liberated p-formylbenzaldoxime, p-formylbenzyl formate mono-p-formylstilbene and mono-p-formyldiphenyl formate, respectively, in high yields. The polymer-bound 1,3-diol groups were regenerated and re-used without significant loss of capacity.