(6Z,9Z)-6,9-dodecadien-1-yne and a process for preparing the same

US11780791B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-11780791-B2
Application numberUS-202217718376-A
CountryUS
Kind codeB2
Filing dateApr 12, 2022
Priority dateApr 14, 2021
Publication dateOct 10, 2023
Grant dateOct 10, 2023

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  1. Title

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  2. Abstract

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  3. Assignees and inventors

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  4. Key dates

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  5. First independent claim

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  6. CPC / IPC classifications

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Abstract

Official abstract text for this publication.

The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1).

First claim

Opening claim text (preview).

The invention claimed is: 1. (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1): 2. A process for preparing (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1): the process comprising: reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2): wherein X represents a halogen atom with a metal acetylide of the following general formula (3): MC≡CH  (3) wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1). 3. A process for preparing (8Z,11Z)-8,11-tetradecadien-3-yn-1-ol of the following formula (4): the process comprising: reacting (6Z,9Z)-6,9-dodecadien-1-yne (1) with a base; and subjecting a reaction mixture thus obtained to a homologation reaction with ethylene oxide to form (8Z,11Z)-8,11-tetradecadien-3-yn-1-ol (4). 4. A process for preparing (3E,8Z,11Z)-3,8,11-tetradecatrien-1-ol of the following formula (5): the process comprising: the process according to claim 3 for preparing (8Z,11Z)-8,11-tetradecadien-3-yn-1-ol (4); and subjecting (8Z,11Z)-8,11-tetradecadien-3-yn-1-ol (4) to a reduction reaction to form (3E,8Z,11Z)-3,8,11-tetradecatrien-1-ol (5), wherein the reduction reaction is carried out using (i) reduction with an organoaluminum compound, (ii) Birch reduction, (iii) ammonia-free Birch reduction, or (iv) Benkeser reduction. 5. A process for preparing (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate of the following formula (6): wherein Ac represents an acetyl group, the process comprising: the process according to claim 4 for preparing (3E,8Z,11Z)-3,8,11-tetradecatrien-1-ol (5); and acetylating (3E,8Z,11Z)-3,8,11-tetradecatrien-1-ol (5) to form (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate (6).

Assignees

Inventors

Classifications

  • C07C11/28Primary

    containing carbon-to-carbon double bonds and carbon-to-carbon triple bonds · CPC title

  • the non-hydrocarbon contains only halogen as hetero-atoms · CPC title

  • by hydrogenation of carbon-to-carbon double or triple bonds · CPC title

  • increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon double or triple bond (C07C29/16 takes precedence) · CPC title

  • Acyclic alcohols with carbon-to-carbon double bonds · CPC title

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What does patent US11780791B2 cover?
The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), w…
Who is the assignee on this patent?
Shinetsu Chemical Co
What technology area does this patent fall under?
Primary CPC classification C07C11/28. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Oct 10 2023 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 6 related publications on this page (citations in our corpus or others sharing the same primary CPC).