PERCHLORIC ACID ISOMERIZATION OF OLEIC ACID

被引：32

作者：

SHOWELL, JS

SWERN, D

NOBLE, WR

机构：

[1] National Science Foundation, Washington, D. C. 20550.

[2] Fels Research Institute, Department of Chemistry, Temple University, Philadelphia

[3] Eastern Regional Research Laboratory, Philadelphia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 07期

关键词：

D O I：

10.1021/jo01271a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

γ-Stearolactone was prepared from oleic acid using 70% perchloric acid in place of the concentrated sulfuric acid customarily used. Improved yields were obtained and the crude reaction product was easier to purify. Isomerization, addition, and polymerization reactions were all found to be important in this process. The procedure is applicable to other olefinic acids, monohydroxy acids, and the methyl esters of olefinic acids. δ-Stearolactone and di- and triestolides were the important intermediates in the production of γ-stearolactone. Other compounds isolated from the final product were the cyclic ketones, 2-tridecyl-2-cyclopentenone and 2-dodecyl-2-cyclohexenone, methyl branched C18 γ-lactones, produced by isomerization of the hydrocarbon chain prior to lactone formation, and δ-stearolactone. © 1968, American Chemical Society. All rights reserved.

引用

页码：2697 / &

共 26 条

[1] ORGANIC REACTIONS IN STRONG ALKALIS .1. FISSION OF ETHYLENIC ACIDS (THE VARRENTRAPP REACTION) [J].