文献类型：期刊文献

英文题名：Ion-exchange-resin-catalyzed adamantylation of phenol derivatives with adamantanols: Developing a clean process for synthesis of 2-(1-adamantyl)-4-bromophenol, a key intermediate of adapalene

作者：Wang, Nan[1];Wang, Ronghua[1];Shi, Xia[1];Zou, Gang[1]

机构：[1]E China Univ Sci & Technol, Dept Fine Chem, Shanghai 200237, Peoples R China

年份：2012

卷号：8

起止页码：227

外文期刊名：BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000300108400001)】；

基金：Financial support provided by the National Science Foundation of China (20972049) is gratefully acknowledged.

语种：英文

外文关键词：adamantylation; ion-exchange resin; phenol; recycling

摘要：A clean process has been developed for the synthesis of 2-adamantylphenol derivatives through adamantylation of substituted phenols with adamantanols catalyzed by commercially available and recyclable ion-exchange sulfonic acid resin in acetic acid. The sole byproduct of the adamantylation reaction, namely water, could be converted into the solvent acetic acid by addition of a slight excess of acetic anhydride during the work-up procedure, making the process waste-free except for regeneration of the ion-exchange resin, and facilitating the recycling of the resin catalyst. The ion-exchange sulfonic acid resin catalyst could be readily recycled by filtration and directly reused at least ten times without a significant loss of activity. The key intermediate of adapalene, 2-(1-adamantyl)-4-bromophenol, could be produced by means of this waste-free process.