Process for preparing diene
US-12103898-B2 · Oct 1, 2024 · US
US11780791B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11780791-B2 |
| Application number | US-202217718376-A |
| Country | US |
| Kind code | B2 |
| Filing date | Apr 12, 2022 |
| Priority date | Apr 14, 2021 |
| Publication date | Oct 10, 2023 |
| Grant date | Oct 10, 2023 |
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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).
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).
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