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A facile synthesis of ethyl 2,4‐dimethoxy‐6‐perfluoroalkyl‐benzoates via acyclic precursors
Author(s) -
Cao WeiGuo,
Shi ZhiJian,
Fan Chun,
Sun RuShu
Publication year - 2004
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.20040221023
Subject(s) - chemistry , yield (engineering) , anhydrous , benzoates , medicinal chemistry , proton nmr , benzene , intramolecular force , molar ratio , ethyl benzoate , organic chemistry , nmr spectra database , spectral line , catalysis , materials science , metallurgy , physics , astronomy
The acyclic precursors. methyl 3‐perfluoroallkyl‐4‐carbethoxy‐5‐methoxy‐6‐(trihenylphosphoranylidene)hexa‐2.4‐dienoates (4) were obtained via the addition reaction of ethyl 3‐methoxy‐4‐(triphenylphosphoranylidene)but‐2‐enoate (2) with equally molar methyl 2‐perfluoroalkynoates (3). Ethyl 2,4‐dimethoxy‐6‐perfluoroalkylbenzoates (5) were synthesized in high yield via an intramolecular elimination of Ph 3 PO of 4 by heating in anhydrous benzene in a sealed tube. The structure of these compounds was confirmed by IR, 1 H, 13 C, 2D C‐H cosy NMR and mass spectra and elemental analyses. The possible reaction mechanisms were also proposed.