A new efficient method for the preparation of intermediate aromatic ketones by Friedel-Crafts acylation

被引：21

作者：

Jin, Xiaojun ^{[1
]}

Wang, Ailing ^{[1
,3
]}

Cao, Hongyu ^{[2
,3
]}

Zhang, Shujia ^{[1
]}

Wang, Lihao ^{[1
]}

Zheng, Xueliang ^{[1
]}

Zheng, Xuefang ^{[2
,3
]}

机构：

[1] Dalian Univ, Dept Chem Engn, Dalian 116622, Peoples R China

[2] Dalian Univ, Coll Bioengn, Dalian 116622, Peoples R China

[3] Dalian Univ, Liaoning Key Lab Bioorgan Chem, Dalian 116622, Peoples R China

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2018年 / 44卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Aromatic ketones; Friedel-Crafts; Acylation; Deep eutectic solvent; DEEP EUTECTIC SOLVENTS; IONIC LIQUIDS; CARBOXYLIC-ACIDS; TRIFLATE; CATALYST; TOLUENE; ARENES;

D O I：

10.1007/s11164-018-3437-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As the most important method to prepare pharmaceutical and chemical intermediate aromatic ketones, Friedel-Crafts (F-C) acylation is used to seek a novel catalytic system which is imminently consistent with the concept of green chemistry. In this study, six deep eutectic solvents (DES) were synthesized for the Friedel-Crafts acylation reaction as a catalytic solvent. Among the six DES, choline chloride-zinc chloride ([ChCl][ZnCl2](2)) proved to be the most competent candidate of electron-rich arenes with acylation reagent. It got the highest yield when 1.0 equivalent of [ChCl][ZnCl2](2) used with acyl halides at 70 degrees C. Recycled DES was reused directly without any extra process. After five cycles, the catalytic activity did not decrease significantly (80-85%). Finally, according to experimental validation, the possible mechanism of this reaction was considered. [GRAPHICS] .

引用

页码：5521 / 5530

页数：10

共 34 条

[21] Mesopore wall-catalyzed Friedel-Crafts acylation of bulky aromatic compounds in MFI zeolite nanosponge [J].

Kim, Jeong-Chul ;

Cho, Kanghee ;

Lee, Sungjune ;

Ryoo, Ryong .

CATALYSIS TODAY, 2015, 243 :103-108

[22] Friedel-Crafts acylation and related reactions catalysed by heteropoly acids [J].

Kozhevnikov, IV .

APPLIED CATALYSIS A-GENERAL, 2003, 256 (1-2) :3-18

[23] A comparative study on iron modified or unmodified tungstophosphoric acid supported on titania for Friedel-Crafts acylation [J].

Mu, Manman ;

Chen, Ligong ;

Wang, Shutao .

JOURNAL OF POROUS MATERIALS, 2015, 22 (05) :1137-1143

[24] Esters as Acylating Reagent in a Friedel-Crafts Reaction: Indium Tribromide Catalyzed Acylation of Arenes Using Dimethylchlorosilane [J].

Nishimoto, Yoshihiro ;

Babu, Srinivasarao Arulananda ;

Yasuda, Makoto ;

Baba, Akio .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9465-9468

[25] Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation [J].

Phuong Hoang Tran ;

Hansen, Poul Erik ;

Hai Truong Nguyen ;

Thach Ngoc Le .

TETRAHEDRON LETTERS, 2015, 56 (04) :612-618

[26] Studies on the plasticization efficiency of deep eutectic solvent in suppressing the crystallinity of corn starch based polymer electrolytes [J].

Ramesh, S. ;

Shanti, R. ;

Morris, Ezra .

CARBOHYDRATE POLYMERS, 2012, 87 (01) :701-706

[27] Use of solid catalysts in Friedel-Crafts acylation reactions [J].

Sartori, G ;

Maggi, R .

CHEMICAL REVIEWS, 2006, 106 (03) :1077-1104

[28] Deep Eutectic Solvents (DESs) and Their Applications [J].

Smith, Emma L. ;

Abbott, Andrew P. ;

Ryder, Karl S. .

CHEMICAL REVIEWS, 2014, 114 (21) :11060-11082

[29] 1-ethyl-3-methylimidazolium halogenoaluminate melts as reaction media for the Friedel-Crafts acylation of ferrocene [J].

Surette, JKD ;

Green, L ;

Singer, RD .

CHEMICAL COMMUNICATIONS, 1996, (24) :2753-2754

[30] Deep eutectic solvent catalyzed Friedel-Crafts alkylation of electron-rich arenes with aldehydes [J].

Wang, Ailing ;

Xing, Pengfei ;

Zheng, Xueliang ;

Cao, Hongyu ;

Yang, Guang ;

Zheng, Xuefang .

RSC ADVANCES, 2015, 5 (73) :59022-59026

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