Preparation of New 2,3-Diphenylpropenoic Acid Esters – Good Yields Even for the More Hindered Z Isomers 英文参考文献.docVIP
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Preparation of New 2,3-Diphenylpropenoic Acid Esters – Good Yields Even for the More Hindered Z Isomers 英文参考文献
Molecules 2004, 9, 256-263
molecules
ISSN 1420-3049
Preparation of New 2,3-Diphenylpropenoic Acid Esters – Good
Yields Even for the More Hindered Z Isomers
László Boros, Károly Felf?ldi and István Pálinkó*
Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720 Hungary, Tel.
(+36) 62 544 288, Fax (+36) 62 544 200.
*Author to whom correspondence should be addressed; e-mail: palinko@chem.u-szeged.hu
Received: 8 March 2004 / Accepted: 18 March 2004 / Published: 31 March 2004
Abstract: The potassium salt of E- and Z-2,3-diphenylpropenoic acids prepared in situ
could be esterified efficiently in DMSO with the appropriate alkyl halides at room
temperature. In this way 10 previously undescribed esters of these acids were synthesised
and characterised. Excellent yields were observed for most of the E isomers and the more
hindered Z esters were also obtained in good yields, far better than those obtained
applying the classical acid-catalysed esterification reaction.
Keywords: Esterification of E- and Z-2,3-diphenylpropenoic acids; DMSO/KOH/alkyl
halide reactant
Introduction
According to published accounts, the acid-catalysed esterification reaction can be conveniently
used for preparing various esters of E-2,3-diphenylpropenoic acid (E-1), while it is not applicable for
the Z isomer (Z-1), due to steric congestion in the transition state [1, 2]. For illustration purposes the
reactivities of the two isomers were studied under the acid-catalysed esterification conditions and
compared to that of the saturated analogue, 2,3-diphenylpropionic acid (Table 1).
Molecules 2004, 9
257
Table 1. Esterification by the CH3OH/H2SO4/reflux method a
Reaction
Acid
Yield %a
time h
0.5
4
2,3-Diphenylpropionic acid
E-2,3-Diphenylpropenoic acid
Z-2,3-Diphenylpropenoic acid
94
77
17
15
aSee Experimental part
It can be seen that the reactivities of the unsaturated acids were lower than those of
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