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Clean Synthesis in Water: Darzens Condensation Reaction of Aromatic Aldehydes with Phenacyl Chloride
Author(s) -
DaQing Shi,
Shu Zhang,
QiYa Zhuang,
XiangShan Wang,
ShuJiang Tu,
HongWen Hu
Publication year - 2003
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20030210620
Subject(s) - chemistry , condensation , chloride , phenacyl , organic chemistry , condensation reaction , epoxy , proton nmr , catalysis , physics , thermodynamics
The Darzens condensation reaction of aromatic aldehydes with phenacyl chloride proceeded very efficiently in a water suspension medium in the presence of triethylbenzylammonium chloride and only trans ‐2, 3‐epoxy‐l, 3‐diaryl‐l‐propanones were formed which can be isolated simply by filtration. The structures of these compounds were confirmed by elemental analysis, IR and 1 H NMR spectra. Their configurations are in agreement with that of the same compounds reported in the literature. Compared to the classical Darzens condensation, this new method has the advantages of good yields, high stereoselectivity, low running cost inexpensive and environmentally benign procedure.