51503-33-4Relevant academic research and scientific papers
Ozonolysis of Olefins, II; Linseed Oil as a Renewable Resource for Alkyl 3,3-Dialkoxypropanoates
Mittelbach, Martin,Poklukar, Norbert
, p. 331 - 332 (2007/10/02)
A new approach to the synthesis of alkyl 3,3-dialkoxypropanoates, which are important intermediates in organic synthesis, starting from fatty esters is described.Thus, ozonolysis of methyl linoleate and methyl linolenate in alcoholic hydrogen chloride affords a reaction mixture, from out of which the alkyl 3,3-dialkoxypropanoates can be isolated by fractional distillation in 60-65percent yield.Even linseed oil, which contains high amounts of linolic and linolenic acid, can be used as starting material, after conversion into the methyl esters by methanolysis.Byproducts of the ozonolysis can be oxidized to the corresponding carboxylic acids which are valuable intermediates in oleochemistry.
A Highly Stereoselective Synthesis of (E)-Enol Lactones by the Wittig Reaction of Cyclic Anhydrides with (α-Alkoxycarbonylethylidene)triphenylphosphorane
Tsuboi, Sadao,Fukumoto, Hirohumi,Wada, Hiroshi,Takeda, Akira,Fukuyama, Keiichi
, p. 689 - 696 (2007/10/02)
Reactions of glutaric anhydride and methyl- or phenyl-substituted ones with (α-alkoxycarbonylethylidene)triphenylphosphorane (2a, ethoxy; 2b, t-butoxy) gave the corresponding 6-alkoxycarbonyl-5-hepten-5-olides (3) and 6-alkoxycarbonyl-4-hepten-5-olides in good yields.The reaction proceeded highly stereoselectively to give (E)-3.The stereochemistry of 3 was determined by an X-ray crystallographic analysis.The reaction of adipic anhydride with 2a afforded 7-ethoxycarbonyl-5-octen-6-olide, 7-ethoxycarbonyl-5,6-octadienoic acid, and (4E,6E)-7-ethoxycarbonyl-4,6-octadienoic acid.A treatment of nonanedioic anhydride with 2a gave 10-ethoxycarbonyl-8,9-undecadienoic acid, (7E,9E)-10-ethoxycarbonyl-7,9-undecadienoic acid, and diethyl 2-methyl-2,4-undecadienedioate in low yields.
