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Azimjon
U. Choriev, Anvar K. Abdushukurov
Chloracetylation of methoxyphenols, synthesis and
subsequent transformations
Abstract
Abstract.
Synthesis and regrouping reaction of 2-methoxyphenylchloracetate in the
presence of small quantities of catalysts were investigated. In the result of
this reaction o- and p-hydroxyphenylchlorides were obtained.
Method of meta-methoxyphenylchloracetate obtain was developed and it was
shown that it can be obtain by chloracetylation of meta-methoxyphenol in
benzol solution. For the first time regrouping of meta-methoxyphenylchloracetate
in the presence of small quantities of FeCl3, MoCl5, WCl6,
ZnCl2, SnCl4, VCl3, FeCl3·6H2O,
Fe2(SO4)3, FAA (ferrum
acetylacetonat), FSA (ferrum salisylat) was carried out. In
the result of this reaction 2-hydroxy-4-methoxyphenacylchloride and
4-hydroxy-2-methoxyphenacylchloride were obtained. The percentage ratio of
obtained isomers depends on the conditions of carrying out of the reaction.
Study of the synthesis 4- methoxyphenylchloroacetate and it’s of the reaction
diphenyltiokarbazone in presence of dimethylformamide. The structure of the
obtained materials are installed by means of UF-, IR- and NMR- spectroscopy.
Key words:
2-methoxyphenylchloroacetate, 2-hydroxy-3-methoxyphenacylchlorid,
Chloracetylation, Fries rearrangement, Lewis acids, meta-methoxyphenylchloroacetate,
2-hydroxy-4-methoxyphenacylchlorid, 4-ìethoxyphenylchloroacetate,
diphenyltio-karbazone, nucleophilic substitution, dimethylformamide,
spectroscopy
Copyright (C) Chemistry Dept., Moscow State University, 2002
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