JPS56167637A - Preparation of 7,11-hexadecadienyl acetate - Google Patents
Preparation of 7,11-hexadecadienyl acetateInfo
- Publication number
- JPS56167637A JPS56167637A JP7174080A JP7174080A JPS56167637A JP S56167637 A JPS56167637 A JP S56167637A JP 7174080 A JP7174080 A JP 7174080A JP 7174080 A JP7174080 A JP 7174080A JP S56167637 A JPS56167637 A JP S56167637A
- Authority
- JP
- Japan
- Prior art keywords
- octene
- halo
- lindlar catalyst
- octyne
- dibromo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To obtain the titled compound useful for sex pheromone substance of pink bollworms, readily and in high yield, by the preparation of a 1-halo-3-octene and 1,8-dibromo-1-octyne as raw materials, then acetylation and further partial hydrogenation in the presence of a Lindlar catalyst.
CONSTITUTION: A 1-halo-3-octene expressed by the formula (X is halogen) is reacted with metallic magnesium to prepare a Grignard reagent, which is then reacted with a 1,8-dibromo-1-octyne to form a 1-bromo-hexadec-11-en-7-yne. The resultant substance is acetylated and further partially hydrogenated in the presence of a Lindlar catalyst, to give the aimed compound. A 1-halo-3-octene as the raw material is obtained by the halogenation of cis-3-octen-1-ol prepared by the partial catalytic hydrogenation of 3-octyn-1-ol in the presence of the Lindlar catalyst. The resultant halide is transformed to the trans isomer by heat-treating in the presence of metallic selenium, and a mixture of cis and trans isomers is obtained. Therefore, the aimed compound is given in a mixture of the (Z,Z)-form with the (Z,E)-form.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7174080A JPS56167637A (en) | 1980-05-29 | 1980-05-29 | Preparation of 7,11-hexadecadienyl acetate |
DE8181103926T DE3165969D1 (en) | 1980-05-26 | 1981-05-21 | Alkynyl halide compounds and alkenyl acetate compounds therefrom |
EP81103926A EP0040829B1 (en) | 1980-05-26 | 1981-05-21 | Alkynyl halide compounds and alkenyl acetate compounds therefrom |
US06/266,614 US4391984A (en) | 1980-05-26 | 1981-05-22 | Alkynyl halide compounds and alkenyl acetate compounds therefrom |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7174080A JPS56167637A (en) | 1980-05-29 | 1980-05-29 | Preparation of 7,11-hexadecadienyl acetate |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS56167637A true JPS56167637A (en) | 1981-12-23 |
JPS6118539B2 JPS6118539B2 (en) | 1986-05-13 |
Family
ID=13469218
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7174080A Granted JPS56167637A (en) | 1980-05-26 | 1980-05-29 | Preparation of 7,11-hexadecadienyl acetate |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS56167637A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH036996Y2 (en) * | 1984-11-08 | 1991-02-21 | ||
JPS6415798A (en) * | 1987-07-09 | 1989-01-19 | Matsushita Electric Ind Co Ltd | Expression apparatus for electronic musical instrument |
JPS6468796A (en) * | 1987-09-09 | 1989-03-14 | Matsushita Electric Ind Co Ltd | Expression apparatus for electronic musical instrument |
-
1980
- 1980-05-29 JP JP7174080A patent/JPS56167637A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6118539B2 (en) | 1986-05-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Savu et al. | Selective. gamma. alkylation of copper enolates derived from. alpha.,. beta.-unsaturated acids: factors affecting scope and regio-and stereoselectivity | |
Hoye et al. | Mercuric trifluoroacetate mediated brominative cyclizations of dienes. Total synthesis of dl-3. beta.-bromo-8-epicaparrapi oxide | |
JPS56167637A (en) | Preparation of 7,11-hexadecadienyl acetate | |
House et al. | Iodolactonization of 3-(3-Cyclohexenyl) propionic Acid1a | |
GB2226312A (en) | 2-Fluoro-5-Bromophenol useful in the production of pesticides | |
US3692851A (en) | 1-Halo-3,7,7,11,11-PENTAMETHYLDI-AND TRI-ENES | |
Ranu et al. | A convenient synthesis of β, γ-unsaturated ketones through zinc-mediated allylation of acid chlorides | |
Sato et al. | Syntheses of female sex pheromone analogues of the German cockroach and their biological activity | |
US3749736A (en) | 5-ethers of 1,3-benzoxathiol-2-one | |
Smith Jr et al. | Teucrium depressum seed oil: A new source of fatty acids with Δ‐‐unsaturation | |
Goto et al. | A stereoselective synthesis of (Z, E)-9, 11-tetradecadienyl-1-acetate, a major component of the sex pheromone of Spodoptera litura | |
JPS56100727A (en) | Cis-6-undecene-1-chloride and its preparation | |
Haubenstock | Stereoselectivities of lithium aluminum trialkoxyhydrides | |
Ono et al. | Regio-and stero-selective γ-substitution of allylic nitro compounds with lithium dialkylcuprates | |
GB1001826A (en) | Improvements in or relating to a tetrahydropyran derivative | |
US2849491A (en) | 6, 8-dimethyl-5-nonen-2-one | |
JPH08119924A (en) | Isomerization of 3,7-dimethyl-2,6-octadienenitrile | |
Akhtar et al. | 190. Studies with acetylenes. Part III. The synthesis of three partly-cis-diphenyloctatetraenes | |
US2833812A (en) | Carboxylic acid esters of cis-3, 6, 7-trimethyl-2-octen-1-ol | |
JPS5724392A (en) | Preparation of alkynyl compound | |
JPS5673032A (en) | 1-halo-4-decene compound | |
Tomida et al. | Preparation of four geometric isomers of 6, 11-hexadecadienal and their flutter stimulating activities on the male eri-silk moth, Philosamia cynthia ricini | |
Ward et al. | Synthesis of acetals by alkylation of 1, 1‐diethoxy‐2‐propyne | |
JPS56120627A (en) | Selective reduction of compound having acetylenic unsaturated bond | |
US2819316A (en) | Synthesis of vitamin a isomers |