Synthesis of Benzyl Phenol from Benzyl Aryl Ether by Polyphosphoric Acid-Catalyzed Benzyl Rearrangement

doi:10.6023/cjoc201901042

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2515-2524.DOI: 10.6023/cjoc201901042 Previous Articles Next Articles

ARTICLE

多聚磷酸催化的苄基芳基醚合成苄基酚的重排反应

刘竺云^a,b, 徐娟娟^a, 凌斌^b, 厉彦翔^b, 刘广聪^b, 王立中^b, 周国春^a

a 南京工业大学药学院南京 211816;
b 泰州职业技术学院药学院泰州 225300

收稿日期:2019-01-26 修回日期:2019-04-30 发布日期:2019-05-15
通讯作者: 周国春 E-mail:gczhou@njtech.edu.cn
基金资助:
江苏省高等学校自然科学研究面上项目（Nos.18KJD350002，17KJB350012）、2018年江苏高校"青蓝工程"优秀青年骨干教师、2018年江苏省高等学校大学生创新创业训练计划（No.201812106004Y）、2017年泰州市科技支撑项目（No.TS201711）、泰州职业技术学院博硕基金（No.TZYBS-17-1）和泰州职业技术学院科研（No.TZYKY-18-28）资助项目.

Synthesis of Benzyl Phenol from Benzyl Aryl Ether by Polyphosphoric Acid-Catalyzed Benzyl Rearrangement

Liu Zhuyun^a,b, Xu Juanjuan^a, Ling Bin^b, Li Yanxiang^b, Liu Guangcong^b, Wang Lizhong^b, Zhou Guochun^a

a School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816;
b School of Pharmacy, Taizhou Polytechnic College, Taizhou 225300

Received:2019-01-26 Revised:2019-04-30 Published:2019-05-15
Contact: 10.6023/cjoc201901042 E-mail:gczhou@njtech.edu.cn
Supported by:
Project supported by the Natural Science Research General Project of Jiangsu Higher Education Institutions (Nos. 18KJD350002, 17KJB350012), the Excellent Young Backbone Teachers of "Blue Project" in Jiangsu Universities in 2018, the College Students' Innovation and Entrepreneurship Training Program in Jiangsu Province in 2018 (No. 201812106004Y), the Science and Technology Support Program of Taizhou (No. TS201711), the Doctoral and Master's Fund of Taizhou Polytechnic College (No. TZYBS-17-1) and the Research Project of Taizhou Polytechnic College (No. TZYKY-18-28).

1. Synthesis of Benzyl Phenol from Benzyl Aryl Ether by Polyphosphoric Acid-Catalyzed Benzyl Rearrangement.PDF(2938KB)

Abstract

The rearrangement activity of benzyl aryl ether catalyzed by polyphosphoric acid (PPA) was systematically investigated. Optimal structural tuning of substitutions of electron withdrawing group (EWG) and electron donating group (EDG) at phenolic moiety or benzyl moiety benefits the rearrangement and the regio-selectivity of the rearrangement obeyed the substitution directing rule at the aromatic ring. This readily available rearrangement method is of practical interest for the benzylation of diverse aromatic phenols.

Key words: polyphosphoric acid (PPA), rearrangement, deprotection, benzyl aryl ether, benzyl phenol

Cite this article

Liu Zhuyun, Xu Juanjuan, Ling Bin, Li Yanxiang, Liu Guangcong, Wang Lizhong, Zhou Guochun. Synthesis of Benzyl Phenol from Benzyl Aryl Ether by Polyphosphoric Acid-Catalyzed Benzyl Rearrangement[J]. Chin. J. Org. Chem., 2019, 39(9): 2515-2524.

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多聚磷酸催化的苄基芳基醚合成苄基酚的重排反应

Synthesis of Benzyl Phenol from Benzyl Aryl Ether by Polyphosphoric Acid-Catalyzed Benzyl Rearrangement

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