Facile 1,2-aryl migration of 2-halomethyl-2-(4'-hydroxyphenyl) ketals: A novel single step synthesis of 4-hydroxyphenylacetic acid & its derivatives.

被引:5
作者
Kumar, A [1 ]
Rane, RA [1 ]
Ravindran, VK [1 ]
Dike, SY [1 ]
机构
[1] ICI INDIA RES & TECHNOL CTR,THANA 400601,MAHARASHTRA,INDIA
关键词
D O I
10.1080/00397919708003348
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2-Aryl migration of 1-halomethyl-2-(4-hydroxyphenyl) ketals, obtained from 2-bromoethyl 4-hydroxyacetophenone, under mild basic conditions have been shown to give 4-hydroxyphenylacetic acidor its derivtives which are key intermediates in the preparation of Atenolol, a well known cardiac beta-blocker.
引用
收藏
页码:1133 / 1141
页数:9
相关论文
共 17 条
[1]  
BARRETT AM, 1970, Patent No. 2007751
[2]   FORMATION OF ARYLACETIC ACIDS, ARYLACETAMIDES, AND ARYLDIHYDROPYRROLES FROM AROMATIC ALDEHYDES [J].
BREEN, L ;
EASTWOOD, FW ;
OCKMAN, T ;
RAE, ID ;
REDWOOD, AM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1973, 26 (10) :2221-2227
[3]   TARTARIC ACID, AN EFFICIENT CHIRAL AUXILIARY - NEW ASYMMETRIC-SYNTHESIS OF 2-ALKYL-2-ARYLACETIC ACIDS [J].
CASTALDI, G ;
CAVICCHIOLI, S ;
GIORDANO, C ;
UGGERI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :3018-3027
[4]  
COOPER MJ, 1980, Patent No. 1576332
[5]  
COPELAND RJ, 1981, Patent No. 1576331
[6]   OXYDATIVER ABBAU ALPHA-SUBSTITUIERTER CARBONSAUREN [J].
FEICHTINGER, H .
CHEMISCHE BERICHTE-RECUEIL, 1962, 95 (09) :2238-&
[7]   SYNTHESIS OF ANTI-INFLAMMATORY ALPHA-ARYLALKANOIC ACIDS BY 1,2-ARYL SHIFT [J].
GIORDANO, C ;
CASTALDI, G ;
UGGERI, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (06) :413-419
[8]  
Mitchell A, 1982, Br. Patent, Patent No. [2 078 718, 2078718]
[9]  
NAKAJIMA K, 1982, Patent No. 2486623
[10]   SELECTIVE BROMINATION OF SUBSTITUTED ACETOPHENONES WITH DIOXAN DIBROMIDE [J].
PASARIBU, SJ ;
WILLIAMS, LR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1973, 26 (06) :1327-1331