Cyclic fatty acid monomers: synthesis and characterization of methyl ω-(2-alkylcyclopentyl) alkenoates and alkanoates

✍ Scribed by J.M. Vatèla; J.L. Sébédio; J.L. Le Quéré

• Book ID: 103040184
• Publisher: Elsevier Science
• Year: 1988
• Tongue: English
• Weight: 680 KB
• Volume: 48
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(88)90139-9

✦ Synopsis

Some 1,2-disubstituted cyclopentanes were synthesized. These were methyl 9-(2-butyl-cyclopentyl)-8-nonenoate, methyl 7-(2hexyl-cyclopentyl)-6-heptenoate and methyl 5-(2-octyl-cyclopentyl)-4-pentenoate and their corresponding alkanoates. The synthesis involved a Michael addition of alkylmagnesium bromide to an unsaturated cyclic ester. The resulting cis and trans ethyl 2-alkylcyclopentane carboxylate were further converted to the alcohols then to the aldehydes. The aldehydes were condensed with the ylide derived from the (¢o-carboxyalkyl)-triphenylphosphonium bromide and methylsulfinylmethide in DMSO to give unsaturated C18 cyclic fatty acid monomers. These cyclic fatty acids were further converted to the methyl esters and the ethylenic bond was reduced by catalytic hydrogenation to give the saturated esters. All the steps were monitored by gas-liqnid chromatography (GLC), J3C-and Jr-nuclear magnetic resonance (NMR), mass spectrometry coupled with GLC (GC-MS) and infra-red spectroscopy (IR).