CN115850026A - Method for synthesizing 5-hexene-1-alcohol - Google Patents
Method for synthesizing 5-hexene-1-alcohol Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 33
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims abstract description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000243 solution Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 239000012074 organic phase Substances 0.000 claims abstract description 21
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims abstract description 20
- 238000001035 drying Methods 0.000 claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000008346 aqueous phase Substances 0.000 claims abstract description 11
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims abstract description 11
- RIMXEJYJXDBLIE-UHFFFAOYSA-N 6-bromohex-1-ene Chemical compound BrCCCCC=C RIMXEJYJXDBLIE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 235000011056 potassium acetate Nutrition 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 239000012071 phase Substances 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 230000007062 hydrolysis Effects 0.000 claims abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 230000035484 reaction time Effects 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 3
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000012141 concentrate Substances 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 13
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- -1 folyl alcohol Chemical compound 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- ASKDFGVMJZMYEM-UHFFFAOYSA-N methyl hex-5-enoate Chemical compound COC(=O)CCCC=C ASKDFGVMJZMYEM-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002085 enols Chemical class 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- GOQJMMHTSOQIEI-UHFFFAOYSA-N hex-5-yn-1-ol Chemical compound OCCCCC#C GOQJMMHTSOQIEI-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
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Abstract
The invention discloses a method for synthesizing 5-hexene-1-alcohol, relating to the technical field of 5-hexene-1-alcohol preparation and comprising the following steps: heating 6-bromo-1-hexene serving as a raw material and tetrabutylammonium bromide serving as a catalyst in an acetonitrile solvent to react with potassium acetate completely; cooling the mixed solution to room temperature (18-25 deg.C), concentrating the reaction solution under reduced pressure, concentrating until no drop occurs, and dissolving in water; adding methyl tert-butyl ether, stirring, separating, extracting the water layer with methyl tert-butyl ether, mixing the organic phases, filtering, and concentrating the filtrate under reduced pressure; the concentrated solution starts to hydrolyze, 15 percent of alkaline aqueous solution and methanol are added into the concentrated solution, and the mixture is stirred and dissolved at normal temperature; after hydrolysis, methanol was concentrated under reduced pressure. After concentration and drying, the system begins to be layered, an upper organic phase and a lower aqueous phase; the water phase is extracted twice by dichloromethane, and the combined organic phases are decompressed and concentrated to obtain the 5-hexene-1-alcohol, which has the beneficial effects that: the method has the advantages of simple reaction conditions, short reaction time, simple process, easy realization and lower cost.
Description
Technical Field
The invention relates to the technical field of 5-hexene-1-alcohol preparation, in particular to a method for synthesizing 5-hexene-1-alcohol.
Background
Enol is an important fine chemical, such as isophytol, folyl alcohol and the like, and can be further used as a key intermediate for synthesizing medicines, pesticides, essences, spices and the like with high economic added values (Chinese Journal of Catalysis,2021,42, 2105-2121), and has large market demand. The invention is environment-friendly and economical, and has important significance in realizing industrial production.
5-hexen-1-ol is a common organic synthesis intermediate and a medical intermediate, and is also an important raw material for chemical engineering and medicine. The scheme for synthesizing the 5-hexene-1-alcohol mainly comprises the following steps: in the first scheme, (Angewandte Chemie-International Edition,2019, vol.58, #4, p.1129-1133) 5-hexen-1-ol is synthesized by reduction with methyl 5-hexenoate or 5-hexenoic acid; in the second scheme, (U.S. Pat. No. 4,88642,1981) 5-hexen-1-ol is synthesized by 1,6-hexanediol; scheme III (WO 2022/19921, 2022) Synthesis of 5-hexen-1-ol with 2- (indolylmethyl) tetrahydropyran; scheme IV (CN 114249629) uses 5-hexyne-1-alcohol to carry out hydrogenation reaction to obtain 5-hexene-1-alcohol.
However, the existing methods for synthesizing 5-hexen-1-ol all have certain disadvantages. Scheme I, 5-hexenoic acid methyl ester or 5-hexenoic acid is used for reduction synthesis of 5-hexenyl-1-ol, raw materials are not easy to obtain, the yield reported by reduction documents is not high, a plurality of byproducts are generated, and purification is difficult.
Scheme II: the method needs high temperature of 300 ℃ for reaction operation, and has high reaction temperature and low yield.
The third scheme is as follows: the process uses 2- (indolylmethyl) tetrahydropyran as a starting material, which is expensive and not readily available.
And the scheme is as follows: the method uses a PdZn/Meso _ S-C catalyst to poison Pd active sites, so that the selectivity of an enol product is improved at the cost of reducing the activity of the catalyst. However, the catalyst not only sacrifices the utilization rate of the active metal Pd, but also pollutes the environment by poisoning agents Pb, quinoline and the like, and the stability of the catalyst is poor.
To this end, we propose a process for the synthesis of 5-hexen-1-ol.
Disclosure of Invention
In view of the deficiencies of the prior art, the present invention provides a method for synthesizing 5-hexen-1-ol, which solves the problems set forth in the background art above.
In order to achieve the purpose, the invention is realized by the following technical scheme: a method for synthesizing 5-hexen-1-ol, characterized in that: the method comprises the following steps:
s1, heating and reacting 6-bromo-1-hexene serving as a raw material with tetrabutylammonium bromide serving as a catalyst in an acetonitrile solvent to react with potassium acetate completely;
s2, cooling the mixed solution to room temperature (18-25 ℃), concentrating the reaction solution under reduced pressure, and adding water to dissolve the reaction solution until the reaction solution is not dripped;
s3, adding methyl tert-butyl ether, stirring, separating, extracting the water layer once with the methyl tert-butyl ether, combining the organic phases, filtering, and concentrating the filtrate under reduced pressure;
s4, starting hydrolysis of the concentrated solution, adding a 15% alkaline aqueous solution and methanol into the concentrated solution, and stirring and dissolving at normal temperature;
and S5, after the hydrolysis is finished, starting to concentrate the methanol under reduced pressure. After concentration and drying, the system begins to be layered, an upper organic phase and a lower aqueous phase;
s6, extracting the water phase twice with dichloromethane, combining the organic phases, and concentrating under reduced pressure to obtain the 5-hexene-1-alcohol.
Alternatively in the present invention, the tetrabutylammonium bromide may be replaced with tetrabutylammonium chloride.
In the invention, the methyl tert-butyl ether can be replaced by dichloromethane and ethyl acetate.
In the invention, the alkaline aqueous solution optionally comprises sodium hydroxide aqueous solution, potassium hydroxide aqueous solution and ammonia aqueous solution.
Alternatively in the present invention, the 6-bromo-1-hexene: tetrabutylammonium bromide: potassium acetate: methyl t-butyl ether: the proportion of the alkaline aqueous solution is 10-15: 1:12 to 20:22 to 29:10 to 15.
In the invention, optionally, the heating temperature of the reaction liquid mixed in the step S1 is 78-83 ℃, and the reaction time is 2 hours.
In the invention, the product prepared in the S1 is 5-alkenyl hexyl ester.
The invention provides a method for synthesizing 5-hexene-1-alcohol, which has the following beneficial effects:
1. the method for synthesizing the 5-hexene-1-alcohol takes the 6-bromine-1-hexene as a raw material and tetrabutylammonium bromide as a catalyst, the used method has the advantages of simple reaction condition, short reaction time, simple process, easy realization and lower cost, and is suitable for the synthesis method for industrially producing the 5-hexene-1-alcohol, wherein acetonitrile is one of the most common organic solvents in an organic laboratory, potassium acetate is a raw material with low price, the reaction condition is simple, the purity of the prepared 5-hexene-1-alcohol is high, the post-reaction treatment is very simple, the production cost is greatly reduced, and the method has stronger economic practicability and flexibility.
2. According to the method for synthesizing the 5-hexenyl-1-ol, 6-bromo-1-hexene is used as a raw material, so that the problems of reduction of 5-hexenoic acid methyl ester or 5-hexenoic acid by a strong metal reducing agent in the method I and hydrogenation reaction of 5-hexyne-1-ol in the method IV can be effectively avoided, hydrogen generation and hydrogen use in the process are avoided, the hydrogenation belongs to high-risk process operation, the safety risk is high, and the production accident is easy to generate; compared with the existing 5-hexene-1-alcohol synthesis method, the method for synthesizing 5-hexene-1-alcohol has the advantages that the conditions are very mild, the safety and operability can be greatly improved, and the industrial production can be conveniently and rapidly carried out.
Drawings
FIG. 1 shows nuclear magnetic hydrogen spectrum of the present invention
FIG. 2 is a schematic view of example 1 of the present invention;
FIG. 3 is a schematic view of example 2 of the present invention;
FIG. 4 is a schematic view of example 3 of the present invention;
fig. 5 is a schematic diagram of embodiment 4 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Referring to fig. 1-5, the present invention provides a technical solution: a method for synthesizing 5-hexene-1-alcohol,
example 1
200.0g of 6-bromo-1-hexene and 39.4g of tetrabutylammonium bromide were dissolved in 400ml of acetonitrile, 144.0g of potassium acetate was added, the mixture was heated to 82 ℃ and refluxed, and completion of the reaction was detected after 2 hours. The mixture was cooled to 20 ℃ and then concentrated to dryness under reduced pressure, 400ml of aqueous clear solution was added to the concentrate, 200ml of methyl tert-butyl ether was added thereto and the mixture was stirred for separation, and the aqueous phase was extracted once with 100ml of methyl tert-butyl ether. And combining organic phases, drying, filtering a system, and concentrating and drying filtrate under reduced pressure to obtain the 5-alkenyl hexyl ester.
5-Enohexyl ester was dissolved in 300ml of methanol solution at 25 ℃ and 331.5g of 15% sodium hydroxide was added thereto to react for 2 hours to detect completion of the reaction. The system begins to concentrate methanol, and after concentration and drying, the system begins to separate into an upper organic phase and a lower aqueous phase. And extracting the water phase twice with dichloromethane, combining the organic phases, concentrating under reduced pressure, and concentrating to dryness to obtain the target product. The yield reaches 82.4 percent, and the purity reaches 99.7 percent. (10:1:12:22:10)
Example 2
60.0g of 6-bromo-1-hexene, 7.88g of tetrabutylammonium bromide were dissolved in 80ml of acetonitrile, 48.02g of potassium acetate was added, the mixture was heated to 82 ℃ and refluxed for 2 hours, and the reaction was detected to be complete. The mixture was cooled to 20 ℃ and then concentrated to dryness under reduced pressure, 80ml of water-soluble supernatant was added to the concentrate, 40ml of methyl t-butyl ether was added thereto and the mixture was stirred for separation, and the aqueous phase was extracted once with 40ml of methyl t-butyl ether. And combining organic phases, drying, filtering a system, and concentrating and drying filtrate under reduced pressure to obtain the 5-alkenyl hexyl ester.
At 25 ℃, 5-alkenyl hexyl ester is dissolved in 70ml of methanol solution, 98.0g of 15% sodium hydroxide is added, and the reaction is detected to be complete after 2 hours of reaction. The system begins to concentrate methanol, and after concentration and drying, the system begins to separate into an upper organic phase and a lower aqueous phase. And extracting the water phase twice with dichloromethane, combining the organic phases, concentrating under reduced pressure, and concentrating to dryness to obtain the target product. The yield reaches 82.0 percent, and the purity reaches 99.3 percent. (15:1:20:30:15)
Example 3
200.0g of 6-bromo-1-hexene and 34.19g of tetrabutylammonium chloride were dissolved in 400ml of acetonitrile, 144.0g of potassium acetate was added, the mixture was heated to 82 ℃ and refluxed, and the completion of the reaction was detected after 2 hours. The mixture was cooled to 20 ℃ and then concentrated to dryness under reduced pressure, 400ml of aqueous solution was added to the concentrate, 200ml of methyl tert-butyl ether was added thereto and the mixture was stirred for separation, and the aqueous phase was extracted once with 100ml of methyl tert-butyl ether. And combining organic phases, drying, filtering a system, and concentrating and drying filtrate under reduced pressure to obtain the 5-alkenyl hexyl ester.
5-Enohexyl ester was dissolved in 300ml of a methanol solution at 25 ℃ and 462.93g of 15% potassium hydroxide were added thereto to complete the reaction for 2 hours. The system begins to concentrate methanol, and after concentration and drying, the system begins to separate into an upper organic phase and a lower aqueous phase. And extracting the water phase twice with dichloromethane, combining the organic phases, concentrating under reduced pressure, and concentrating to dryness to obtain the target product. The yield reaches 78 percent, and the purity reaches 99.8 percent. (10:1:12:22:10)
Example 4
200.0g of 6-bromo-1-hexene, 39.4g of tetrabutylammonium bromide were dissolved in 400ml of acetonitrile, 144.0g of potassium acetate was added, the mixture was heated to 82 ℃ and refluxed, and the reaction was detected to be complete after 2 hours. The mixture was cooled to 20 ℃ and then concentrated to dryness under reduced pressure, 400ml of aqueous clear solution was added to the concentrate, 200ml of dichloromethane was added thereto and the mixture was stirred for separation, and the aqueous phase was extracted once with 90ml of dichloromethane. And combining organic phases, drying, filtering a system, and concentrating and drying filtrate under reduced pressure to obtain the 5-alkenyl hexyl ester.
5-Enohexyl ester was dissolved in 300ml of methanol solution at 25 ℃ and 331.5g of 15% sodium hydroxide was added thereto to react for 2 hours to detect completion of the reaction. The system begins to concentrate methanol, and after concentration and drying, the system begins to separate into an upper organic phase and a lower aqueous phase. And extracting the water phase twice with dichloromethane, combining the organic phases, concentrating under reduced pressure, and concentrating to dryness to obtain the target product. The yield reaches 76 percent, and the purity reaches 99.1 percent. (10:1:12:22:10)
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (7)
1. A method for synthesizing 5-hexen-1-ol, characterized in that: the method comprises the following steps:
s1, heating 6-bromo-1-hexene serving as a raw material and tetrabutylammonium bromide serving as a catalyst in an acetonitrile solvent to react with potassium acetate completely;
s2, cooling the mixed solution to room temperature (18-25 ℃), concentrating the reaction solution under reduced pressure, and adding water to dissolve the reaction solution until the reaction solution is not dripped;
s3, adding methyl tert-butyl ether, stirring, separating, extracting the water layer once with the methyl tert-butyl ether, combining the organic phases, filtering, and concentrating the filtrate under reduced pressure;
s4, starting hydrolysis of the concentrated solution, adding a 15% alkaline aqueous solution and methanol into the concentrated solution, and stirring and dissolving at normal temperature;
and S5, after the hydrolysis is finished, starting to concentrate the methanol under reduced pressure. After the concentration and drying, the system begins to layer, an upper organic phase and a lower aqueous phase;
s6, extracting the water phase twice with dichloromethane, combining the organic phases, and concentrating under reduced pressure to obtain the 5-hexene-1-alcohol.
2. The method of synthesizing 5-hexen-1-ol according to claim 1, characterized in that: the tetrabutylammonium bromide can be replaced by tetrabutylammonium chloride.
3. The process for the synthesis of 5-hexen-1-ol according to claim 1, characterized in that: the methyl tert-butyl ether can be replaced by dichloromethane and ethyl acetate.
4. The method of synthesizing 5-hexen-1-ol according to claim 1, characterized in that: the alkaline aqueous solution comprises a sodium hydroxide aqueous solution, a potassium hydroxide aqueous solution and an ammonia aqueous solution.
5. The method of synthesizing 5-hexen-1-ol according to claim 1, characterized in that: the ratio of 6-bromo-1-hexene: tetrabutylammonium bromide: potassium acetate: methyl tert-butyl ether: the proportion of the alkaline aqueous solution is 10-15: 1:12 to 20:22 to 29:10 to 15.
6. The method of synthesizing 5-hexen-1-ol according to claim 1, characterized in that: the heating temperature of the reaction liquid mixed in the S1 is 78-83 ℃, and the reaction time is 2 hours.
7. The method of synthesizing 5-hexen-1-ol according to claim 1, characterized in that: the product prepared in the S1 is 5-alkenyl hexyl ester.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060069288A1 (en) * | 2004-05-25 | 2006-03-30 | Southard Glen E | Process for preparing vinyl substituted beta-diketones |
| CN105175219A (en) * | 2015-08-05 | 2015-12-23 | 山东成泰化工有限公司 | Synthesis method of prenyl alcohol |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060069288A1 (en) * | 2004-05-25 | 2006-03-30 | Southard Glen E | Process for preparing vinyl substituted beta-diketones |
| CN105175219A (en) * | 2015-08-05 | 2015-12-23 | 山东成泰化工有限公司 | Synthesis method of prenyl alcohol |
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