Citation: 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]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2515-2524. doi: 10.6023/cjoc201901042 shu

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

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

Corresponding author: Zhou Guochun, gczhou@njtech.edu.cn
Received Date: 26 January 2019
Revised Date: 30 April 2019
Available Online: 15 September 2019
Fund Project: the Doctoral and Master's Fund of Taizhou Polytechnic College TZYBS-17-1the Research Project of Taizhou Polytechnic College TZYKY-18-28the Natural Science Research General Project of Jiangsu Higher Education Institutions 17KJB350012the Science and Technology Support Program of Taizhou TS201711the 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 201812106004YProject 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)the Natural Science Research General Project of Jiangsu Higher Education Institutions 18KJD350002

Figures(1)

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.
- polyphosphoric acid (PPA),
- rearrangement,
- deprotection,
- benzyl aryl ether,
- benzyl phenol
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