pTSA-catalyzed condensation of xylenols and aldehydes under solvent-free conditions: One-pot synthesis of 9H-xanthene or bisphenol derivatives
作者:Akbar Mobinikhaledi、Hassan Moghanian、Maryam Deinavizadeh
DOI:10.1016/j.crci.2013.03.008
日期:2013.11
Résumé A simple and efficient procedure for the synthesis of 9H-xanthene or bisphenol derivatives has been developed by one-pot condensation of xylenols with aromatic aldehydes in the presence of p-toluenesulfonic acid (pTSA) as a catalyst under solvent-free conditions at 100 °C. It is noteworthy that the condensation reaction of 3,5-xylenol with aldehydes produces 9H-xanthene derivatives, while the reaction with other xylenols leads to the corresponding bisphenol derivatives. Different types of aromatic aldehydes are used in the reaction and in every case the products were obtained in good to excellent yields. The structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR and CHN data.
摘要
开发了一种简单高效的合成9H-呕吐酮或双酚衍生物的方法,该方法通过在无溶剂条件下以p-甲苯磺酸(pTSA)作为催化剂,在100°C下对二甲苯酚与芳香醛进行一锅法缩合反应。需要注意的是,3,5-二甲基苯酚与芳香醛的缩合反应生成9H-呕吐酮衍生物,而与其他二甲基苯酚的反应则导致相应的双酚衍生物。反应中使用了不同类型的芳香醛,且在每种情况下产品的收率均良好到优异。根据红外光谱(IR)、氢核磁共振(1H NMR)、碳核磁共振(13C NMR)及元素分析(CHN)数据确定了这些化合物的结构。