caa a22 4500 465765432 CHVBK 20180323111912.0 cr unu---uuuuu 170327e19900101xx s 000 0 eng 10.1007/BF02562419 doi (NATIONALLICENCE)springer-10.1007/BF02562419 A study of the structures and reactions of some methyl substituted unsaturated C18 ester intermediates in the synthesis of a racemic mixture of 10-methyloctadecanoic acid [Elektronische Daten] [Marcel Lie, Ken Jie, David Leung] Methyl 10-undecenoate was hydrated to methyl 10-hydroxyundecanoate using mercury (II) acetate in aqueous tetrahydrofuran (THF). Chromic acid oxidation of methyl 10-hydroxyundecanoate gave methyl 10-oxoundecanoate, which was hydrolyzed to 10-oxoundecanoic acid. Reaction of n-octyl magnesium bromide complex in THF with 10-oxoundecanoic acid furnished 10-hydroxy-10-methyloctadecanoic acid after hydrolysis. The latter compound was esterified, and dehydration of methyl 10-hydroxy-10-methyloctadecanoate withp-toluenesulfonic acid in benzene gave a mixture of unsaturated branched fatty ester intermediates:viz. methyl 10-methyl-9-octadecenoate, 10-methyl-10-octadecenoate and 10-octyl-10-undecenoate. Treatment of the mixture of unsaturated branched fatty ester intermediates with mercury (II) acetate in methanol gave exclusively methyl 10-methoxy-10-methyloctadecanoate. Epoxidation of the same mixture of unsaturated fatty esters withm-chloroperbenzoic acid provided a mixture of epoxy derivatives: methyl 9,10-epoxy-10-methyloctadecanoate, 10,11-epoxy-10-methyloctadecanoate and 2-octyl-oxirane-nonanoate. Catalytic hydrogenation of the mixture of unsaturated fatty esters gave a racemic mixture of methyl 10-methyloctadecanoate, which was hydrolyzed to 10-methyloctadecanoic acid. The structures of the mixture of unsaturated branched fatty ester intermediates and their derivatives were characterized by chemical and spectroscopic analyses. the American Oil Chemists' Society (AOCS), 1990 Lie Marcel Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut Jie Ken Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut Leung David Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut Lipids Springer-Verlag 25/1(1990-01-01), 1-5 0024-4201 25:1<1 1990 25 11745 https://doi.org/10.1007/BF02562419 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02562419 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Lie Marcel Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut NATIONALLICENCE 700 1- Jie Ken Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut NATIONALLICENCE 700 1- Leung David Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut NATIONALLICENCE 773 0- Lipids Springer-Verlag 25/1(1990-01-01), 1-5 0024-4201 25:1<1 1990 25 11745 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer