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Article: Ultrasound in fatty acid chemistry: synthesis of a novel 1-pyrroline fatty ester isomer from methyl ricinoleate

TitleUltrasound in fatty acid chemistry: synthesis of a novel 1-pyrroline fatty ester isomer from methyl ricinoleate
Authors
Issue Date1994
PublisherA O C S Press. The Journal's web site is located at http://www.aocs.org/press/lipids.htm
Citation
Lipids, 1994, v. 29, p. 889-892 How to Cite?
AbstractA novel 1-pyrroline fatty acid ester isomer (viz. 8-5-hexyl-1-pyrrolin-2-yl) octanoate) has been synthesized from methyl ricinoleate by two routes with an overall yield of 42 and 30%, respectively. Most of the reactions are carried out under concomitant ultrasonic irradiation (20 KHz, ca. 53 watts/cm2). Under such a reaction condition, the reaction time is considerably shortened, and product yields are high. Dehydrobromination under concomitant ultrasonic irradiation of methyl 9, 10-dibromo-12-hydroxyoctadecanoate with KOH in EtOH furnishes methyl 12-hydroxy-9-octadecynoate (66%) within 15 min. Hydration of the latter under ultrasound with mercury(II)acetate in aqueous tetrahydrofuran yields exclusively methyl 12-hydroxy-9-oxo-octadecanoate (95%) in 30 min. The hydroxy group in the latter compound is transformed to the azido function via the mesylate, and treatment of the azido-oxo intermediate (methyl 12-azido-9-oxooctadecanoate) with Ph3P under ultrasonic irradiation furnishes the requisite 1-pyrroline fatty acid ester (77%). The same azido-oxo intermediate has also been obtained by the oxidation of methyl 12-azido-9-cis-octadecenoate using benzoquinone and a catalytic amount of Pd(II)chloride in aqueous tetrahydrofuran under concomitant ultrasonic irradiation (90 min) to give the product in 45% yield. The latter reaction does not take place even under prolonged silent stirring of the reaction mixture.
Persistent Identifierhttp://hdl.handle.net/10722/209160
ISSN
2015 Impact Factor: 1.892
2015 SCImago Journal Rankings: 0.795

 

DC FieldValueLanguage
dc.contributor.authorLie Ken Jie, MSF-
dc.contributor.authorSyed Rahmatullah, MSK-
dc.contributor.authorLam, CK-
dc.contributor.authorKalluri, P-
dc.date.accessioned2015-04-01T07:03:15Z-
dc.date.available2015-04-01T07:03:15Z-
dc.date.issued1994-
dc.identifier.citationLipids, 1994, v. 29, p. 889-892-
dc.identifier.issn0024-4201-
dc.identifier.urihttp://hdl.handle.net/10722/209160-
dc.description.abstractA novel 1-pyrroline fatty acid ester isomer (viz. 8-5-hexyl-1-pyrrolin-2-yl) octanoate) has been synthesized from methyl ricinoleate by two routes with an overall yield of 42 and 30%, respectively. Most of the reactions are carried out under concomitant ultrasonic irradiation (20 KHz, ca. 53 watts/cm2). Under such a reaction condition, the reaction time is considerably shortened, and product yields are high. Dehydrobromination under concomitant ultrasonic irradiation of methyl 9, 10-dibromo-12-hydroxyoctadecanoate with KOH in EtOH furnishes methyl 12-hydroxy-9-octadecynoate (66%) within 15 min. Hydration of the latter under ultrasound with mercury(II)acetate in aqueous tetrahydrofuran yields exclusively methyl 12-hydroxy-9-oxo-octadecanoate (95%) in 30 min. The hydroxy group in the latter compound is transformed to the azido function via the mesylate, and treatment of the azido-oxo intermediate (methyl 12-azido-9-oxooctadecanoate) with Ph3P under ultrasonic irradiation furnishes the requisite 1-pyrroline fatty acid ester (77%). The same azido-oxo intermediate has also been obtained by the oxidation of methyl 12-azido-9-cis-octadecenoate using benzoquinone and a catalytic amount of Pd(II)chloride in aqueous tetrahydrofuran under concomitant ultrasonic irradiation (90 min) to give the product in 45% yield. The latter reaction does not take place even under prolonged silent stirring of the reaction mixture.-
dc.languageeng-
dc.publisherA O C S Press. The Journal's web site is located at http://www.aocs.org/press/lipids.htm-
dc.relation.ispartofLipids-
dc.titleUltrasound in fatty acid chemistry: synthesis of a novel 1-pyrroline fatty ester isomer from methyl ricinoleate-
dc.typeArticle-
dc.identifier.emailLie Ken Jie, MSF: hrsclkj@hku.hk-
dc.identifier.pmid7854016-
dc.identifier.hkuros515-
dc.identifier.volume29-
dc.identifier.spage889-
dc.identifier.epage892-
dc.publisher.placeUnited States-

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