Conversion of Methyl Oleate to Branched-Chain Derivatives

Autor:	Nicolette T. Prevost, Oliver D. Dailey
Rok vydání:	2007
Předmět:	Methyl oleate Allylic rearrangement General Chemical Engineering Organic Chemistry chemistry.chemical_element Grignard reagent Branched chain fatty acids Crystallization temperature Oleic acid chemistry.chemical_compound Differential scanning calorimetry chemistry Organic chemistry Lithium
Zdroj:	Journal of the American Oil Chemists' Society. 84:565-571
ISSN:	1558-9331 0003-021X
DOI:	10.1007/s11746-007-1077-x
Popis:	Studies were conducted in the synthetic conversion of oleic acid to mid-chain branched fatty acids. Methyl oleate was brominated in the allylic positions. Reaction of the allylic bromides with lithium dimethylcuprate gave primarily the desired branched-chain derivatives (93% of product mixture). The product had a significantly lower crystallization temperature in comparison with methyl oleate. Reaction of the allylic bromides with lithium di-n-butylcuprate or lithium di-sec-butylcuprate also gave branched-chain derivatives, but in this instance there was the complication of attack on the ester functionality in the fashion of a Grignard reagent. Details of the syntheses and the properties of the products (with emphasis on low-temperature properties) are discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::42e8a79eeb844af4b4c0a0ea830950e8 https://doi.org/10.1007/s11746-007-1077-x Zobrazit plný text záznamu Full text from SpringerLink Plný text