Synthesis of vinyl threo‐9, 10‐threo‐12, 13‐tetrahydroxystearates

Autor:	G. E. McManis, John C Cowan, W. J. Dejarlais, L. E. Gast, John L. O舗Donnell
Rok vydání:	1967
Předmět:	Boric acid chemistry.chemical_compound Hydrolysis Degree of unsaturation chemistry General Chemical Engineering Organic Chemistry Acetone Infrared spectroscopy Organic chemistry Boron trifluoride Derivative (chemistry) Catalysis
Zdroj:	Journal of the American Oil Chemists' Society. 44:652-655
ISSN:	1558-9331 0003-021X
DOI:	10.1007/bf02680036
Popis:	Methyl esters from vernonia oil containingcis-12,13-epoxy-cis-9-octadecenoate were reacted with acetone in the presence of a boron trifluoride catalyst to yieldtrans-12,13-0-isopropylidene-9-ene derivative I. Epoxidation of the unsaturation followed by reaction with acetone gave the isomerictrans,trans-di-0-isopropylidene deriva-tivesIII of 9,10 :12,13-tetrahydroxystearates. The carboxylic acids of III were converted to vinyl esters and subsequent hydrolysis of the isopropy-lidene groups with boric acid produced vinylthreo-9,10threo-12,13-tetrahydroxystearates. By the same sequence of reactions monoepoxidized methyl linoleate yielded an optically inactive de-rivative which had identical refractive index, IR spectrum, and GLC data toIII from vernonia methyl esters.
Databáze:	OpenAIRE
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