Industrial & Engineering Chemistry Research, Vol.49, No.7, 3106-3111, 2010
Synthesis of beta-Amino Alcohols from Methyl Epoxy Stearate
Oils and fats are an important source of renewable raw materials, and the availability of functionalized fatty acids such as epoxy ring containing fatty acids gives us a convenient source of starting materials for the synthesis of various biodegradable derivatives. Methyl esters of the epoxidized oleic acid [methyl 9,10-epoxy octadecanoate (1)] on the catalytic epoxy ring opening reaction with various aliphatic [butyl (2), octyl (3)], cyclic [pyrrolidine (4), piperidine (5), morpholine (6)], and aromatic [p-chloroaniline (7), p-anisidine (8), benzyl amine (9), aniline (10)] amines resulted in the formation of the respective beta-amino alcohols [methyl 9-(butylamino)-10-hydroxyoctadecanoate (11a)/methyl 10-(butylamino)-9-hydroxyoctadecanoate (11b), methy 10-hydroxy-9-(octylamino)octadecanoate (12a)/methyl 9-hydroxy-10-(octylamino)octadecanoate (12b), methyl 10-hydroxy-9-(pyrrolidin-1-yl)octadecanoate (13a)/methyl 9-hydroxy-10-(pyrrolidin-1-yl)octadecanoate (13b), methyl 10-hydroxy-9-(piperidin-1-yl)octadecanoate (14a)/methyl 9-hydroxy-10-(piperidin-1-yl)octadecanoate (14b), methyl 10-hydroxy-9-morpholinooctadecanoate (15a)/methyl 9-hydroxy-10-morpholinooctadecanoate (15b), methyl 9-(4-chlorophenylamino)-10-hydroxyoctadecanoate (16a)/methyl 10-(4-chlorophenylamino)9-hydroxyoctadecanoate (16b), methyl 10-hydroxy-9-(4-methoxyphenylamino)octadecanoate (17a)/methyl 9-hydroxy-10-(4-methoxyphenylamino)octadecanoate (17b), methyl 9-(benzylamino)-10-hydroxyoctadecanoate (18a)/methyl 10-(benzylamino)-9-hydroxyoctadecanoate (18b), methyl 10-hydroxy-9-(phenylamino)octadecanoate (19a)/methyl 9-hydroxy-10-(phenylamino)octadecanoate (19b)] as isomeric mixtures. Zinc(II) perchlorate hexahydrate was used as a Lewis acid catalyst to achieve these transformations under solvent-free conditions.