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Article: Ultrasound in fatty acid chemistry: synthesis of a novel 1-pyrroline fatty ester isomer from methyl ricinoleate
Title | Ultrasound in fatty acid chemistry: synthesis of a novel 1-pyrroline fatty ester isomer from methyl ricinoleate |
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Authors | |
Issue Date | 1994 |
Publisher | A 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? |
Abstract | A 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 Identifier | http://hdl.handle.net/10722/209160 |
ISSN | 2023 Impact Factor: 1.8 2023 SCImago Journal Rankings: 0.438 |
DC Field | Value | Language |
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dc.contributor.author | Lie Ken Jie, MSF | - |
dc.contributor.author | Syed Rahmatullah, MSK | - |
dc.contributor.author | Lam, CK | - |
dc.contributor.author | Kalluri, P | - |
dc.date.accessioned | 2015-04-01T07:03:15Z | - |
dc.date.available | 2015-04-01T07:03:15Z | - |
dc.date.issued | 1994 | - |
dc.identifier.citation | Lipids, 1994, v. 29, p. 889-892 | - |
dc.identifier.issn | 0024-4201 | - |
dc.identifier.uri | http://hdl.handle.net/10722/209160 | - |
dc.description.abstract | A 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.language | eng | - |
dc.publisher | A O C S Press. The Journal's web site is located at http://www.aocs.org/press/lipids.htm | - |
dc.relation.ispartof | Lipids | - |
dc.title | Ultrasound in fatty acid chemistry: synthesis of a novel 1-pyrroline fatty ester isomer from methyl ricinoleate | - |
dc.type | Article | - |
dc.identifier.email | Lie Ken Jie, MSF: hrsclkj@hku.hk | - |
dc.identifier.pmid | 7854016 | - |
dc.identifier.hkuros | 515 | - |
dc.identifier.volume | 29 | - |
dc.identifier.spage | 889 | - |
dc.identifier.epage | 892 | - |
dc.publisher.place | United States | - |
dc.identifier.issnl | 0024-4201 | - |