Oxidation of unsaturated compounds. III. Oxidation of 3-chlorocrotonic acid. Synthesis of dl-threonic acid. Proof of configuration of the dl-1,2-dihydroxybutyric acids was written by Braun, Geza. And the article was included in Journal of the American Chemical Society in 1930.Recommanded Product: 26340-58-9 This article mentions the following:
Oxidation of 3-chlorocrotonic acid, m. 83°, with Ba(ClO3)2 in H2O containing a little osmic acid, gives 78% of dl-threo-1,2-dihydroxy-3-chlorobutyric acid (I), m. 100°; further oxidation, after removing the Cl with AcOAg, with dilute HNO3, gives dl-(HC(OH)CO3H)3 and a small amount of (CO3H)3. I, neutralized with BaCO3, and treated with Ag2O, gives 46% of dl-threonic acid, m. 98°; with HNO3 no trace of mesotartaric acid is found, proving that the treatment with HNO3 causes no inversion. This acid does not form a lactone under the conditions in which the dl-erythronic acid can be isolated only as a lactone. The proof of the configuration of the dl-1,2-dihydroxybutyric acids (II) is based on the fact that the I may be converted into racemic acid and on the other hand it may be catalytically reduced to the II, m. 74-5°, in 70% yield. This shows clearly that the II, m. 74°, has the same configuration as racemic acid and the other possible II, m. 81.5°, has a configuration corresponding to mesotartaric acid. The assignment of the prefixes “threo” and “erythro” for the acids m. 74.5° and 81.5°, resp., is therefore justified. In the experiment, the researchers used many compounds, for example, (E)-4-Chlorobut-2-enoic acid (cas: 26340-58-9Recommanded Product: 26340-58-9).
(E)-4-Chlorobut-2-enoic acid (cas: 26340-58-9) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Recommanded Product: 26340-58-9
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics