Fatty acids, part 37: Application of the oxymercuration-demercuration reaction to long-chain unsaturated esters

✍ Scribed by F.D. Gunstone; R.P. Inglis

• Publisher: Elsevier Science
• Year: 1973
• Tongue: English
• Weight: 701 KB
• Volume: 10
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(73)90042-x

✦ Synopsis

Methyl oleate is converted in high yield to methyl 9(10)-methoxystearate by reaction with methanol in the presence of mercuric acetate followed by demercuration with sodium borohydride. Similar ethoxy-, hydroxy-, acetoxy-, acetylamino-, and hydroxyethoxystearates result when the nucleophilic solvent is ethanol, water, acetic acid, acetonitrile, and ethane-l,2-dioi respectively, sometimes in the presence of DMF or THF as co-solvent. Reactions with hydrogen peroxide or with t-butylhydroperoxide are more complex and give several products. Non-participating substituents (OAc, OMe, CO2Me) sufficiently close to the reacting double bond influence the proportion of the two possible oxymercuration products. Reaction with several methyl octadecadienoates and with some seed oils is also reported. * Part 36: Chem. Phys. Lipids 9 (1972) 112.