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Methods for producing 2,6-dimethyl-1,5-heptadien-3-ol and 2,6-dimethyl-1,5-heptadien-3-yl acetate
US10138189B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10138189-B2 |
| Application number | US-201715653393-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 18, 2017 |
| Priority date | Jul 29, 2016 |
| Publication date | Nov 27, 2018 |
| Grant date | Nov 27, 2018 |
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Abstract
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Provided are industrial and economical methods for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate (3), which is, for example, a sex pheromone component of Comstock mealybug, and 2,6-dimethyl-1,5-heptadien-3-ol (2), which is an intermediate of the acetate (3). More specifically, provided are a method for producing 2,6-dimethyl-1,5-heptadien-3-ol comprising a step of subjecting 2-methyl-3-buten-2-yl 2-methyl-2-propenyl ether (1) to a rearrangement reaction in the presence of a base to obtain 2,6-dimethyl-1,5-heptadien-3-ol (2), and a method for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate comprising a step of acetylating the produced 2,6-dimethyl-1,5-heptadien-3-ol (2) to obtain 2,6-dimethyl-1,5-heptadien-3-yl acetate (3).
First claim
Opening claim text (preview).
What is claimed is: 1. A method for producing 2,6-dimethyl-1,5-heptadien-3-ol, comprising a step of subjecting 2-methyl-3-buten-2-yl 2-methyl-2-propenyl ether of formula (1): to a rearrangement reaction in the presence of a base to obtain 2,6-dimethyl-1,5-heptadien-3-ol of formula (2): 2. The method for producing 2,6-dimethyl-1,5-heptadien-3-ol according to claim 1 , wherein the base is selected from the group consisting of metal alkoxides, organometallic compounds, and metal amides. 3. A method for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate, comprising the steps of: subjecting 2-methyl-3-buten-2-yl 2-methyl-2-propenyl ether of formula (1): to a rearrangement reaction in the presence of a base to obtain 2,6-dimethyl-1,5-heptadien-3-ol of formula (2): and acetylating the 2,6-dimethyl-1,5-heptadien-3-ol to obtain 2,6-dimethyl-1,5-heptadien-3-yl acetate of formula (3): wherein Ac represents an acetyl group. 4. The method for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate according to claim 3 , wherein the base is selected from the group consisting of metal alkoxides, organometallic compounds, and metal amides.
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Classifications
by elimination of -OH groups, e.g. by dehydration (C07C29/34 takes precedence) · CPC title
Monocarboxylic acid esters having at least two carbon-to-carbon double bonds · CPC title
- C07C29/56Primary
by isomerisation · CPC title
Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring · CPC title
by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title
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- What does patent US10138189B2 cover?
- Provided are industrial and economical methods for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate (3), which is, for example, a sex pheromone component of Comstock mealybug, and 2,6-dimethyl-1,5-heptadien-3-ol (2), which is an intermediate of the acetate (3). More specifically, provided are a method for producing 2,6-dimethyl-1,5-heptadien-3-ol comprising a step of subjecting 2-methyl-3-bute…
- Who is the assignee on this patent?
- Shinetsu Chemical Co
- What technology area does this patent fall under?
- Primary CPC classification C07C29/56. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Nov 27 2018 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 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).