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

Author
Organization
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).
Keywords
12-E, METHYL 9-OXO-10, E-OCTADECADIENOATE, CYCLOHEXYL 9-OXO-10, CATALYSIS

Citation

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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.
@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},
}

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