Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates
Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates
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DOI：
10.1002/adsc.201900287
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发表时间：
2019-08
影响因子：
5.4
通讯作者：
Shih-Chieh Kao;Yi‐Ching Lin;I. Ryu;Yen‐Ku Wu
中科院分区：
文献类型：
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作者：
Shih-Chieh Kao;Yi‐Ching Lin;I. Ryu;Yen‐Ku Wu
描述了一种四丁基氟化铵介导的酚类与环状碳酸酯的羟烷基化反应。这种操作简单的方法能够以良好至优异的产率合成各种芳基β-羟乙基醚，催化剂负载量非常小（0.1-1摩尔%）。 特别值得注意的是芳香族二醇和间苯三酚有效转化为相应的双羟乙基化和三羟乙基化产物。为了进一步展示该方案的多功能性，通过愈创木酚和碳酸甘油酯的缩合用单一步骤制备愈创木酚甘油醚。我们还开发了一个流动乙氧基化过程，允许多花醇的连续合成。
Described is a tetrabutylammonium fluoride‐mediated hydroxyalkylation reaction of phenols with cyclic carbonates. This operationally simple method enables the synthesis of a variety of aryl β‐hydroxyethyl ethers in good to excellent yields with a very small amount of catalyst loading (0.1–1 mol%). Of particular note is the efficient conversion of aromatic diols and phloroglucinol to the corresponding bis‐ and tris‐hydroxyethylated products. To further showcase the versatility of this protocol, guaifenesin was prepared with a single step by the condensation of guaiacol and glycerol carbonate. We also developed a flow ethoxylation process permitting the continuous synthesis of multiflorol.