CHEMOSELECTIVE C-BENZOYLATION OF PHENOLS BY USING ALCl3 UNDER SOLVENT-FREE CONDITIONS

被引:2
作者
Gaikwad, Sunil V. [1 ]
Nawghare, Beena R. [1 ]
Lokhande, Pradeep D. [1 ]
机构
[1] Savitribaiphule Pune Univ, Dept Chem, Pune 411007, Maharashtra, India
关键词
Chemoselective C-acylation; F-C reaction; Fries rearrangement; FRIEDEL-CRAFTS ACYLATION; AROMATIC-COMPOUNDS; EFFICIENT SYNTHESIS; REARRANGEMENT; ACIDS; DEPROTECTION; ANALOGS; COMPLEX; KETONES; KINASE;
D O I
10.4314/bcse.v29i2.14
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2'-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products.
引用
收藏
页码:319 / 325
页数:7
相关论文
共 59 条
[1]  
Arad D, 1999, [No title captured], Patent No. [WO 99/30699, 9930699]
[2]   Design and crystal structures of protein kinase B-selective inhibitors in complex with protein kinase a and mutants [J].
Breitenlechner, CB ;
Friebe, WG ;
Brunet, E ;
Guido, W ;
Graul, M ;
Thomas, U ;
Künkele, KP ;
Schäfer, W ;
Gassel, M ;
Bosseineyer, D ;
Huber, R ;
Engh, RA ;
Masjost, B .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (01) :163-170
[3]   Propionylation of phenol to 4-hydroxypropiophenone over zeolite H-beta [J].
Chaube, VD ;
Moreau, P ;
Finiels, A ;
Ramaswamy, AV ;
Singh, AP .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 174 (1-2) :255-264
[4]   Synthesis of flavanones using nanocrystalline MgO [J].
Choudary, BM ;
Ranganath, KVS ;
Yadav, J ;
Kantam, ML .
TETRAHEDRON LETTERS, 2005, 46 (08) :1369-1371
[5]   ENVIRONMENTALLY FRIENDLY CHEMISTRY USING SUPPORTED REAGENT CATALYSTS - STRUCTURE-PROPERTY RELATIONSHIPS FOR CLAYZIC [J].
CLARK, JH ;
CULLEN, SR ;
BARLOW, SJ ;
BASTOCK, TW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06) :1117-1130
[6]   Fries rearrangement in methane sulfonic acid, an environmental friendly acid [J].
Commarieu, A ;
Hoelderich, W ;
Laffitte, JA ;
Dupont, MP .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 182 (01) :137-141
[7]   ON THE TRANSITION-STATE FOR CLAYZIC-CATALYZED FRIEDEL-CRAFTS REACTIONS UPON ANISOLE [J].
CORNELIS, A ;
LASZLO, P ;
WANG, S .
TETRAHEDRON LETTERS, 1993, 34 (24) :3849-3852
[8]   FRIEDEL-CRAFTS ACYLATIONS WITH MODIFIED CLAYS AS CATALYSTS [J].
CORNELIS, A ;
GERSTMANS, A ;
LASZLO, P ;
MATHY, A ;
ZIEBA, I .
CATALYSIS LETTERS, 1990, 6 (01) :103-110
[9]  
David R., 1993, HDB DATA ORGANIC COM
[10]  
Dean F. M., 1980, J CHEM SOC P1, VI, P1986