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    • Development of 3-methoxy-4-benzyloxybenzyl alcohol (MBBA) resin as polymer-supported synthesis support: Preparation and benzyl ether cleavage by DDQ oxidation

      Qiang Huang Bao-Zhong Zheng Quan Long

      Full Papers Volume 122 Issue 2 March 2010 pp 203-207

    • Fulltext

       

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/122/02/0203-0207

    • Keywords

       

      Solid-phase organic synthesis; polymer support; linker; 3-methoxy-4-benzyloxybenzyl alcohol resin; DDQ oxidation; recycling.

    • Abstract

       

      3-Methoxy-4-benzyloxybenzyl alcohol (MBBA) resin was synthesized by a two-step sequence under microwave irradiation involving the reaction of commercially available Merrifield resin with vanillin, followed by reduction with sodium borohydride. MBBA resin was treated with bromides in the presence of sodium hydride to afford the corresponding resin-bound benzyl ethers. Cleavage of the resin-bound benzyl ethers from the MBBA resin was carried out using 2,3-dichloro-5,6-dicyanobenzoqunone (DDQ) to give the corresponding alcohols in good yields. Moreover, the recovery, regeneration, and reuse of this polymer support could be achieved easily. MBBA resin can be developed as a kind of solid-phase synthesis bead of alcohols.

    • Author Affiliations

       

      Qiang Huang1 Bao-Zhong Zheng1 Quan Long2

      1. Department of Materials Science and Engineering, Yunnan University, Kunming, Yunnan 650091, PR China
      2. School of Chemical Science and Engineering, Yunnan University, Kunming, Yunnan 650091, PR China

    • Dates

       
      Published
      March 2010
      Manuscript received
      17 April 2009
      Manuscript revised
      13 September 2009
      Accepted
      23 December 2009

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