Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1980-03-10
1982-08-31
Shippen, Michael L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
564189, 564201, 260399, 564202, 564205, 2604055, 564209, 564210, 260413, 260465D, 2604654, 562426, 562431, 562468, 562470, 562471, 562472, 562500, 562504, 562505, 562507, 562508, 562510, 562581, 562586, 562587, 562588, 562599, 564123, 564161, 564162, 564171, 564174, 564175, 564181, 564188, 564191, C07C 5100
Patent
active
043473792
ABSTRACT:
Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted. It is now possible to produce, simply and conveniently, numerous substituted alpha-beta monolefinically unsaturated carboxylic acids with a variety of substituents on the alpha carbon atom, and, optionally on the beta carbon atom of these substituted carboxylic acids. Esters may also be conventionally derived from both the 2-alkoxycarboxylic acids, and the unsaturated carboxylic acids.
During the phase transfer catalyzed synthesis of this invention, an intermediate acyl halide derivative is formed prior to the formation of the 2-alkoxycarboxylic acid reaction product. The formation of the acyl halide derivative allows the subsequent direct formation, in a modification of the same reaction, of 2-alkoxycarboxylic acid amides (or "2-alkoxycarbamides"), simply by adding a primary or secondary amine to the reaction mass. By dealkoxylation of the 2-alkoxycarbamides, specific, necessarily alpha-substituted and optionally beta-substituted acrylamides are synthesized which previously could be prepared, if at all, only with difficulty.
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Lobo Alfred D.
Shippen Michael L.
Shust Nestor W.
The B. F. Goodrich Company
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