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Synthesis of the 9-oxodiene derivative of methyl dimorphecolate by an efficient Oppenauer oxidation procedure.

P Tassignon, T Derijk, D Dewit and L Debuyck (1994) CHEMISTRY AND PHYSICS OF LIPIDS. 74(1). p.39-42
abstract
Oxidation of methyl dimorphecolate (1) to methyl 9-oxo-10,12-E,E-octadecadienoate (2) has been studied, using Oppenauer conditions. Acetone and cyclohexanone have been used as oxidizing ketones. Combination of cyclohexanone with inert solvents has been performed to minimize the side reactions: degradation of the aluminum alkoxide catalyst and transesterification of the desired product (2). The optimal procedure is reported on 25 g scale using cyclohexanone (1.5 eq) and aluminum t-butoxide (0.2 eq) in hexane at 50 degrees C (30 min).
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
12-E, METHYL 9-OXO-10, E-OCTADECADIENOATE, CYCLOHEXYL 9-OXO-10, CATALYSIS
journal title
CHEMISTRY AND PHYSICS OF LIPIDS
Chem. Phys. Lipids
volume
74
issue
1
pages
39 - 42
Web of Science type
Article
ISSN
0009-3084
DOI
10.1016/0009-3084(94)90109-0
language
English
UGent publication?
yes
classification
A1
id
200136
handle
http://hdl.handle.net/1854/LU-200136
date created
2004-01-14 13:42:00
date last changed
2016-12-19 15:38:50
@article{200136,
  abstract     = {Oxidation of methyl dimorphecolate (1) to methyl 9-oxo-10,12-E,E-octadecadienoate (2) has been studied, using Oppenauer conditions. Acetone and cyclohexanone have been used as oxidizing ketones. Combination of cyclohexanone with inert solvents has been performed to minimize the side reactions: degradation of the aluminum alkoxide catalyst and transesterification of the desired product (2). The optimal procedure is reported on 25 g scale using cyclohexanone (1.5 eq) and aluminum t-butoxide (0.2 eq) in hexane at 50 degrees C (30 min).},
  author       = {Tassignon, P and Derijk, T and Dewit, D and Debuyck, L},
  issn         = {0009-3084},
  journal      = {CHEMISTRY AND PHYSICS OF LIPIDS},
  keyword      = {12-E,METHYL 9-OXO-10,E-OCTADECADIENOATE,CYCLOHEXYL 9-OXO-10,CATALYSIS},
  language     = {eng},
  number       = {1},
  pages        = {39--42},
  title        = {Synthesis of the 9-oxodiene derivative of methyl dimorphecolate by an efficient Oppenauer oxidation procedure.},
  url          = {http://dx.doi.org/10.1016/0009-3084(94)90109-0},
  volume       = {74},
  year         = {1994},
}

Chicago
Tassignon, P, T Derijk, D Dewit, and L Debuyck. 1994. “Synthesis of the 9-oxodiene Derivative of Methyl Dimorphecolate by an Efficient Oppenauer Oxidation Procedure.” Chemistry and Physics of Lipids 74 (1): 39–42.
APA
Tassignon, P., Derijk, T., Dewit, D., & Debuyck, L. (1994). Synthesis of the 9-oxodiene derivative of methyl dimorphecolate by an efficient Oppenauer oxidation procedure. CHEMISTRY AND PHYSICS OF LIPIDS, 74(1), 39–42.
Vancouver
1.
Tassignon P, Derijk T, Dewit D, Debuyck L. Synthesis of the 9-oxodiene derivative of methyl dimorphecolate by an efficient Oppenauer oxidation procedure. CHEMISTRY AND PHYSICS OF LIPIDS. 1994;74(1):39–42.
MLA
Tassignon, P, T Derijk, D Dewit, et al. “Synthesis of the 9-oxodiene Derivative of Methyl Dimorphecolate by an Efficient Oppenauer Oxidation Procedure.” CHEMISTRY AND PHYSICS OF LIPIDS 74.1 (1994): 39–42. Print.