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The Reaction of Ethyl Bromoacetate with Dimethyl Sulfoxide
Author(s) -
Tien J. M.
Publication year - 1974
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.197400032
Subject(s) - chemistry , bromide , dimethyl sulfide , dimethyl sulfoxide , swern oxidation , ethyl bromoacetate , yield (engineering) , hydrogen bromide , glyoxylate cycle , sulfide , hydrogen sulfide , organic chemistry , ethyl acetate , sulfoxide , medicinal chemistry , bromine , enzyme , sulfur , materials science , metallurgy
The reaction of excess dimethyl sulfoxide with ethyl bromoacetate has been shown to produce ethyl glyoxylate, hydrogen bromide, and dimethyl sulfide. The yield of glyoxylate at first was reduced because the dimethyl sulfide reacted with bromoacetate to form trimethylsulfonium bromide and ethyl (methylmercapto) acetate, presumably via carbethoxymethyldimethylsulfonium bromide. These side reactions were diminished in a thin‐film reactor, but the result was not satisfiable, the yield was 51%, and the side reactions were prevented by addition of methyl bromide, which rapidly consumed the dimethyl sulfide with formation of trimethylsulfonium bromide. Addition of 1, 2‐epoxy‐3‐phenoxypropane removed the hydrogen bromide, thereby preventing the deleterious effects casued by its reduction of dimethyl sulfoxide to dimethyl sulfide. In this way has been developed a convenient preparation of ethyl glyoxylate in yields averaging about 70%. Identification and stoichiometry of the reaction products are presented.