CN103449990A - 4(or 3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde mixture and preparation method thereof - Google Patents
4(or 3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde mixture and preparation method thereof Download PDFInfo
- Publication number
- CN103449990A CN103449990A CN2012101778938A CN201210177893A CN103449990A CN 103449990 A CN103449990 A CN 103449990A CN 2012101778938 A CN2012101778938 A CN 2012101778938A CN 201210177893 A CN201210177893 A CN 201210177893A CN 103449990 A CN103449990 A CN 103449990A
- Authority
- CN
- China
- Prior art keywords
- hydroxy
- methyl
- mixture
- preparation
- cyclohex
- 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.)
- Pending
Links
Abstract
The invention relates to a 4(or 3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde mixture and a novel preparation method thereof.
Description
Technical field
The present invention relates to 4 (or 3)-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde (4 (or3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde) mixture and the novel method for preparing it.
Background of invention
Need to prepare the novel method of perfume molecules in fragrance industry always.Art-recognizedly to the actual consideration such as synthetic, may hinder the use of perfume molecules in commercial applications.Sometimes whether the synthetic of unpredictable appointment perfume molecules can carry out by commercial size.Therefore, the fragrance industry unremitting effort is with the novel and economic method of research and development preparation perfume molecules.
Summary of the invention
4 (or 3) that the present invention relates to be expressed from the next-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde mixture:
Formula I formula II
Its Chinese style I is 4-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde; Formula II is 3-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde.
More specifically, the present invention relates to prepare the novel method of 4 (or 3)-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde mixture.
Can be expressly understood these embodiments of the present invention and other embodiment by reading following specification sheets.
Embodiment
4 (or 3)-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde mixture is commercially available spices.Fragrance of a flower tune, lily of the valley aromatic (muguet note), aldehyde aromatic and the wooden aromatic of this compound are widely used in current perfumed product.But, the synthetic method of report has some shortcomings before, for example use expensive catalyzer, described catalyzer comprises diethylaluminum chloride (Tetrahedron Letters 1999 (40) nb.32,5817-5822), boron trifluoride diethyl etherate (boron trifluoride diethyl etherate) (Zhurnal Organicheskoi Khimii 1981 (17) nb.11,2277-2281 and 2033-2036), zinc chloride (II) (Tetrahedron Letters 2011 (52) nb.52,7157-7160) and other lewis acid catalyst known in the art.
According to the present invention, can prepare 4 (or 3)-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde isomer by following reaction scheme, in an embodiment described reaction scheme is described in detail.Reagent all can commercially availablely be buied.
Wherein " heating " mean that temperature of reaction is for being more than or equal to 50 ℃, preferred 50-160 ℃, more preferably 90-110 ℃.
It will be understood by those skilled in the art that compound of the present invention is comprised of steric isomer and the regional isomer of claimed compound.Compound as herein described comprises the isomer mixture of these compounds, and can by technical point well known by persons skilled in the art from these isomer.For example, suitable technology comprises distillation and chromatography, as is called the high performance liquid chromatography, particularly silica gel column chromatography of HPLC, and gas-chromatography (GC) trapping.But the commercially available prod major part provides with isomer mixture.Those skilled in the art will also be understood that technology well known by persons skilled in the art can obtain the series mixture of different blended composition and division in a proportion as the GOODLOE post with high theoretical tray.
Specific implementations of the present invention below is provided.Other distortion of the present invention will be apparent for a person skilled in the art.Within should be appreciated that these distortion are included in the scope of the invention.Unless otherwise indicated, all percentage ratio used herein is all weight percentage, and g is interpreted as gram, and mol is interpreted as mole.In an embodiment, IFF means international flavouring agent and (the International Flavors& of spices company limited of New York, United States New York; Fragrances Inc., New York, NY, USA).
example I
The preparation of 4 (or 3)-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde mixture: add myrcenol (154g, 1.0mol) and propenal (21g, 0.375mol) in reaction flask, and be heated to 90-110 ℃.Whether by gas-chromatography (GC), analyze monitoring reaction completes.The crude product obtained is distilled, obtained product 4 (or 3)-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde mixture (67g, 0.32mol).
4 (or 3) that more than obtain-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde mixture has fragrance of a flower tune, lily of the valley aromatic, aldehyde aromatic and wooden aromatic.
Claims (2)
1. a method for preparing 4 (or 3)-(4-hydroxy-4-methyl-amyl group)-hexamethylene-3-alkene carboxylic aldehyde mixture, described method comprises the step that myrcenol and propenal are reacted under the temperature condition of 50-160 ℃.
2. the method for claim 1, is characterized in that, described temperature is 90-110 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101778938A CN103449990A (en) | 2012-05-31 | 2012-05-31 | 4(or 3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde mixture and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101778938A CN103449990A (en) | 2012-05-31 | 2012-05-31 | 4(or 3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde mixture and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103449990A true CN103449990A (en) | 2013-12-18 |
Family
ID=49732886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012101778938A Pending CN103449990A (en) | 2012-05-31 | 2012-05-31 | 4(or 3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde mixture and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103449990A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166263A (en) * | 1997-03-27 | 2000-12-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for the manufacture of acrolein |
| US6187963B1 (en) * | 1997-03-27 | 2001-02-13 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for the manufacture of acrolein derivatives |
-
2012
- 2012-05-31 CN CN2012101778938A patent/CN103449990A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166263A (en) * | 1997-03-27 | 2000-12-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for the manufacture of acrolein |
| US6187963B1 (en) * | 1997-03-27 | 2001-02-13 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for the manufacture of acrolein derivatives |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2612975C1 (en) | Method of producing 1,3-butadiene | |
| JP5175539B2 (en) | Cyclohexylalkanol | |
| CN112142592A (en) | Method for synthesizing acetate perfume | |
| BRPI0719754A2 (en) | PYRANE DERIVATIVES, PROCESS FOR PREPARATION AND USE OF THEM IN FRAGRANCE AND FRAGRANCE | |
| CN103449990A (en) | 4(or 3)-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene carbaldehyde mixture and preparation method thereof | |
| JP2010511677A (en) | Use of camphorenic derivatives as aroma components in fragrances and flavorings | |
| CN103524340A (en) | Isopentene acetate and preparation method thereof | |
| JP5501524B1 (en) | Nitrile compounds | |
| CN103524547A (en) | Silica hybrid dehydroherbac and preparing method thereof | |
| CN103449991A (en) | 4(or 3),6-dimethyl-3-cyclohexene-1-carbaldehyde mixture and preparation method thereof | |
| JP2653027B2 (en) | 3- (Hexenyloxy) -propane-nitrile, method for producing the same, fragrance or fragrance composition | |
| CN112624926B (en) | Compound with cinnamon fragrance and preparation method and application thereof | |
| JP2010500421A (en) | Cyclopentane / cyclopentene aldehyde derivatives or cyclopentane / cyclopentene ketone derivatives and their use as scented substances | |
| JP2023513202A (en) | 3-Hexene-1-ol isomer mixture and its preparation process | |
| JP5107694B2 (en) | Aldehyde compounds | |
| CN105061153A (en) | Method for preparing thymol through isopropyl m-cresols | |
| JPS6215552B2 (en) | ||
| JP4033309B2 (en) | Phenoketal and its use as an aromatic substance | |
| CN103508997A (en) | 1,4-dioxacycloheptadecane-5,17-diketone and preparation method thereof | |
| CN103664865A (en) | 5-sec-butyl-2-(2,4-dimethyl-cyclohex-3-enyl)-5-methyl-[1,3]dioxane and process for making the same | |
| JPH08119924A (en) | Isomerization of 3,7-dimethyl-2,6-octadienenitrile | |
| RU2784618C2 (en) | Method of manufacture of organic compounds | |
| CN109651122B (en) | Method for preparing cyclocitral by catalyzing citral conversion with zinc-containing ionic liquid | |
| JP3955628B2 (en) | Carbonyl compounds | |
| WO2013146390A1 (en) | Method for producing 3-alkoxy-3-methyl-1-butanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20131218 |