- A (Z/E) - 8 - dodecene -1 - ethoxylate ester synthesis method
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The invention discloses a (Z/E)-8-dodecylene-1-olacetate synthesis method. The method is characterized in that 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials undergo a coupling reaction to produce 8-(2-oxotetrahydropyranyl)dodecyne, the 8-(2-oxotetrahydropyranyl)dodecyne is subjected to hydrogenation, one-pot deprotection and esterification so that (Z)-8-dodecylene-1-olacetate and (E)-8-dodecylene-1-olacetate are obtained, wherein a mole ratio of (Z)-8-dodecylene-1-olacetate to (E)-8-dodecylene-1-olacetate is (90%-99.5%): (10%-0.5%). The method utilizes 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials, provides a novel reaction route, has a short route, produces less by-product, has simple and routine processes, is free of complex post-reaction treatment processes and improves production efficiency. The method satisfies different insect pheromone trap or lure requirements on an isomer ratio in practical application and is suitable for large-scale industrial production.
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Paragraph 0047-0066
(2018/07/06)
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- SYNTHESIS OF PHEROMONES, III IMPROVED AND STEREOCONTROLLED SYNTHESES OF ISOMERIC MIXTURES OF 8-DODECEN-1-YL ACETATES
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Simple syntheses have been developed for the preparation of isomeric mixtures of 8-dodecen-1-yl acetates, which are active sex pheromones of many insect species.The Wittig reaction under modified conditions and reduction of the C-C triple bond were applied for the stereocontrolled formation of the C-C double bond.
- Vinczer, Peter,Juvanecz, Zoltan,Novak, Lajos,Szantay, Csaba
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p. 737 - 748
(2007/10/02)
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- Metamorphosis of Castor Oil to Insect Sex-pheromones and Useful Synthons
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The primary fragmentation products of Castor oil (1), namely, methyl undec-10-enoate (2) and sebacic acid (3) have been converted, using novel reactions and strategies into synthons of the type H-CC-(CH2)n-3-CH2OTHP (n=6=4; n=7=14; n=8=22; n=9=29).A surprisingly clean decarboxylative elimination of sebacic acid monoester gives methyl non-8-enoate (7), a synthon related to recefeiolide and a precursor to 4, the utility of which, has been illustrated with the synthesis of insect-pheromones of the species Grapholita molesta.Methyl dec-9-enoate (15) has been prepared by a novel and practical terminal ? to lower terminal ? degradation of 2.Compound 7 has been transformed via synthon 14 to the insect sex-pheromones of the species, Spodoptera frugiperda, Heliothis virescens and Paralobesia viteana in high yields and excellent stereochemical purity. 1-Tetrahydropyranyloxyundec-10-yne (22) readily prepared from 2, has been used to illustrate a new strategy in pheromone synthesis, namely, the use of coupling elements, leading to the preparation of bombykol in high yields and excellent stereochemical purity. 1-Tetrahydropyranyloxydodec-11-yne (29), already reported, has been transformed to vaccenic acid (30), the transposed ?-isomer of oleic acid, in good yields, thus demonstrating the use of acetylide synthons for the preparation of rare fatty acids also.
- Ranganathan, S.,Maniktala, Vibha,Kumar, Raaj,Singh, G. P.
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p. 1197 - 1207
(2007/10/02)
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