CN114409519A - Method for synthesizing cis-jasmone - Google Patents
Method for synthesizing cis-jasmone Download PDFInfo
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- CN114409519A CN114409519A CN202111541400.XA CN202111541400A CN114409519A CN 114409519 A CN114409519 A CN 114409519A CN 202111541400 A CN202111541400 A CN 202111541400A CN 114409519 A CN114409519 A CN 114409519A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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Abstract
The invention discloses a method for synthesizing cis-jasmone, which specifically comprises the following steps: performing Grignard reaction on 1, 4-dichlorobutene and methyl magnesium chloride in a THF medium to obtain 1-chloro-2-pentene. 2, 5-hexanedione is subjected to cyclization reaction in a dibromomethane medium under a strong alkaline condition to obtain the 3-methyl-2-cyclopentene-1-ketone. Performing addition/elimination reaction on the 1-chloro-2-pentene and the 3-methyl-2-cyclopentene-1-one in an ethanol medium under an alkaline condition to obtain the cis-jasmone. Compared with other synthesis methods, the method has the advantages of short process route, high reaction selectivity and conversion rate, high product yield, low cost and the like.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, relates to the synthesis of spices, and particularly relates to a method for synthesizing cis-jasmone.
Background
Cis-jasmone, the scientific name of which is 3-methyl-2- (2-pentene) -2-cyclopenten-1-one, is colorless to pale yellow oily liquid, slightly soluble in water, and soluble in ethanol, diethyl ether and carbon tetrachloride. The cis-jasmone is naturally present in jasmine, mint, pepper, spearmint, jonquil, bergamot and tea, and has good diffusibility of flower fragrance and elegant jasmine fragrance. The essence is mainly used as a perfume base of jasmine perfume, is widely applied to jasmine-fragrance daily chemical essence, and various edible essences such as jasmine tea, strawberry, pineapple, mint-fragrance edible essence and the like.
Various methods for synthesizing cis-jasmone are reported, such as: 1. cyclopentene-2-ketone is used as a raw material, firstly, beta-sulfonation is carried out on the cyclopentene-2-ketone and benzene sulfinic acid sodium to obtain 3-sulfonyl cyclopentanone, then, the 3-sulfonyl cyclopentanone and ethylene glycol are condensed under an acidic condition to obtain ketal, then, beta-side chain alkenylation is carried out, and after acidification treatment, aldol condensation is carried out to obtain cis-jasmone. 2. Taking 2-methylfuran as a raw material, firstly condensing with propylene aldehyde under alkaline condition to synthesize 3- (2-methyl-5-furyl) propionaldehyde, then generating 2-methyl-5- (3-hexenyl) furan through Wittig reaction, then opening ring under acidic condition to prepare undecenedione, and finally condensing ring under alkaline condition to obtain cis-jasmone. 3. Taking furfural as a raw material, firstly carrying out a Grignard reaction with cis-2-pentenyl magnesium chloride, acidifying, then carrying out catalytic isomerization to generate cis-2-pentenyl-3-hydroxy-4-cyclopentenone, then carrying out hydrogenation reduction under an acidic condition to obtain cis-2-pentenyl-2-cyclopentenone, and finally carrying out a methylation reaction with methyl iodide to obtain cis-jasmone. The methods have the problems of longer synthesis process route, lower product yield, large amount of three wastes, difficult treatment and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for synthesizing cis-jasmone, which has the advantages of short process route, high reaction selectivity and conversion rate, high product yield and low cost.
The invention is realized by the following technical scheme:
a method for synthesizing cis-jasmone comprises the following steps:
step one, putting 1, 4-dichlorobutene and THF into a reactor in proportion, stirring and heating, dissolving methyl magnesium chloride in THF to form a THF solution, dropwise adding the THF solution into the reactor, controlling the temperature to react after dropwise adding, quenching and hydrolyzing with a saturated ammonium chloride solution when the content of 1, 4-dichlorobutene is less than 1%, adding water to dissolve salt, separating out an organic phase, recovering the solvent THF at normal pressure, and then carrying out reduced pressure rectification to obtain an intermediate product 1-chloro-2-pentene;
step two, putting 2, 5-hexanedione and dibromomethane in a certain proportion into a reactor, stirring, dropwise adding a sodium hydroxide solution, finishing dropping, heating, performing reflux reaction until the content of the 2, 5-hexanedione is less than 1%, cooling, neutralizing and washing, recovering solvent dibromomethane from a separated organic phase at normal pressure, and performing reduced pressure rectification to obtain an intermediate product, namely 3-methyl-2-cyclopentene-1-one;
and step three, putting the 1-chloro-2-pentene obtained in the step one and the 3-methyl-2-cyclopentene-1-ketone obtained in the step two into a reactor in proportion, adding ethanol and sodium hydroxide, stirring, controlling the temperature to react, recovering ethanol at normal pressure when the content of the 3-methyl-2-cyclopentene-1-ketone is less than 1 percent as a reaction end point, neutralizing and washing, and carrying out vacuum rectification on the organic phase to obtain a cis-jasmone finished product.
The reaction equation is as follows:
the invention further improves the scheme as follows:
in the first step, the molar ratio of the 1, 4-dichlorobutene to the methyl magnesium chloride is 1: 1.1-1.3; 1, 4-dichlorobutene and THF are put into a reactor according to the mass ratio of 1: 3; the mass concentration of methyl magnesium chloride in the THF solution was 25%.
Further, in the first step, the 1, 4-dichlorobutene is cis-1, 4-dichlorobutene.
Further, in the first step, the temperature of the temperature-controlled reaction is 20-25 ℃.
Further, in the first step, the recovered solvent THF can be reused.
Further, in the second step, the mass ratio of the 2, 5-hexanedione to the dibromomethane is 1: 3; the molar ratio of the 2, 5-hexanedione to the sodium hydroxide in the sodium hydroxide solution is 1: 1; the mass concentration of the sodium hydroxide is 10%.
Further, in the second step, the recovered solvent dibromomethane can be reused.
Further, in the third step, the molar ratio of the 1-chloro-2-pentene to the 3-methyl-2-cyclopenten-1-one is 1.1-1.3: 1; the mass ratio of the 3-methyl-2-cyclopentene-1-ketone to the ethanol is 1: 3; the mass ratio of the 3-methyl-2-cyclopentene-1-ketone to the sodium hydroxide is 1: 0.5.
Further, in the third step, the temperature-controlled reaction temperature is 30-40 ℃.
Further, in the third step, the recovered solvent ethanol can be reused.
The invention has the beneficial effects that:
compared with other synthesis methods, the method has the advantages of short process route, high reaction selectivity and conversion rate, high product yield, low cost and the like.
Detailed Description
Example 1
125g (1mol) of 1, 4-dichlorobutene and THF375g are put into a reactor, stirred and heated to 20 ℃, 328g (1.1mol) of methyl magnesium chloride (25% THF solution) is slowly dripped, the temperature is controlled at 20-25 ℃ after the dripping is finished, and the stirring reaction is carried out, wherein the reaction end point is when the content of the 1, 4-dichlorobutene is less than 1%. Adding saturated ammonium chloride solution to quench hydrolysis, adding water to dissolve salt, separating out organic phase, recovering solvent THF (for reuse) at normal pressure, and vacuum rectifying to obtain intermediate product 1-chloro-2-pentene. The effective amount of the product is 91g, and the yield is 87.1%.
57g (0.5mol) of 2, 5-hexanedione and 171g of dibromomethane are put into a reactor, stirred, 200g (0.5mol) of 10% sodium hydroxide solution is added dropwise, and the reaction is carried out under reflux at the temperature rising after dropping until the content of the 2, 5-hexanedione is less than 1%. Cooling, neutralizing and washing, recovering solvent dibromomethane (for repeated use) from separated organic phase at normal pressure, and rectifying under reduced pressure to obtain intermediate product 3-methyl-2-cyclopentene-1-ketone. The effective amount of the product is 87g, and the yield is 90.6%.
115g (1.1mol) of intermediate product 1-chloro-2-pentene, 96g (1mol) of intermediate product 3-methyl-2-cyclopentene-1-ketone, 288g of ethanol and 48g of sodium hydroxide are sequentially added into a reactor, stirred and heated, the temperature is controlled at 30-40 ℃ for reaction, and the reaction end point is determined when the content of the 3-methyl-2-cyclopentene-1-ketone is less than 1%. Firstly recovering ethanol under normal pressure (for reuse), then neutralizing and washing, and carrying out vacuum rectification on the organic phase to obtain a cis-jasmone finished product. The effective amount of the product is 129g, and the yield is 78.7%.
Example 2
125g (1mol) of 1, 4-dichlorobutene and THF375g are put into a reactor, stirred and heated to 20 ℃, 358g (1.2mol) of methyl magnesium chloride (25% THF solution) is slowly dripped, the temperature is controlled at 20-25 ℃ after dripping, stirred and reacted, and the reaction end point is determined when the content of the 1, 4-dichlorobutene is less than 1%. Adding saturated ammonium chloride solution to quench hydrolysis, adding water to dissolve salt, separating out organic phase, recovering solvent THF (for reuse) at normal pressure, and vacuum rectifying to obtain intermediate product 1-chloro-2-pentene. The effective amount of the product is 95g, and the yield is 90.9%.
114g (1mol) of 2, 5-hexanedione and 342g of dibromomethane are put into a reactor, stirred, 400g (1mol) of 10% sodium hydroxide solution is added dropwise, and the reaction is carried out under reflux at the end of dropping and heating until the content of the 2, 5-hexanedione is less than 1%. Cooling, neutralizing and washing, recovering solvent dibromomethane (for repeated use) from separated organic phase at normal pressure, and rectifying under reduced pressure to obtain intermediate product 3-methyl-2-cyclopentene-1-ketone. The effective amount of the product is 88g, and the yield is 91.7%.
125g (1.2mol) of intermediate product 1-chloro-2-pentene, 96g (1mol) of intermediate product 3-methyl-2-cyclopentene-1-ketone, 288g of ethanol and 48g of sodium hydroxide are sequentially added into a reactor, stirred and heated, the temperature is controlled at 30-40 ℃ for reaction, and the reaction end point is determined when the content of the 3-methyl-2-cyclopentene-1-ketone is less than 1%. Firstly recovering ethanol under normal pressure (for reuse), then neutralizing and washing, and carrying out vacuum rectification on the organic phase to obtain a cis-jasmone finished product. The effective amount of the product is 132g, and the yield is 80.5%.
Example 3
125g (1mol) of 1, 4-dichlorobutene and THF375g are put into a reactor, stirred and heated to 20 ℃, 388g (1.3mol) of methyl magnesium chloride (25 percent of THF solution) is slowly dripped, the temperature is controlled at 20-25 ℃ after the dripping is finished, and the stirring reaction is carried out, wherein the reaction end point is that the content of the 1, 4-dichlorobutene is less than 1 percent. Adding saturated ammonium chloride solution to quench hydrolysis, adding water to dissolve salt, separating out organic phase, recovering solvent THF (for reuse) at normal pressure, and vacuum rectifying to obtain intermediate product 1-chloro-2-pentene. The effective amount of the product is 92g, and the yield is 88.1%.
171g (1.5mol) of 2, 5-hexanedione and 513g of dibromomethane are put into a reactor, stirred, added with 600g (1.5mol) of 10% sodium hydroxide solution dropwise, heated and refluxed until the content of the 2, 5-hexanedione is less than 1%, and finally reaches the end of the reaction. Cooling, neutralizing and washing, recovering solvent dibromomethane (for repeated use) from separated organic phase at normal pressure, and rectifying under reduced pressure to obtain intermediate product 3-methyl-2-cyclopentene-1-ketone. The effective amount of the product is 86g, and the yield is 89.6%.
136g (1.3mol) of intermediate product 1-chloro-2-pentene, 96g (1mol) of intermediate product 3-methyl-2-cyclopentene-1-ketone, 288g of ethanol and 48g of sodium hydroxide are sequentially added into a reactor, stirred and heated, the temperature is controlled at 30-40 ℃ for reaction, and the reaction end point is determined when the content of the 3-methyl-2-cyclopentene-1-ketone is less than 1%. Firstly recovering ethanol under normal pressure (for reuse), then neutralizing and washing, and carrying out vacuum rectification on the organic phase to obtain a cis-jasmone finished product. The effective amount of the product is 128g, and the yield is 78.1%.
Claims (10)
1. A method for synthesizing cis-jasmone is characterized by comprising the following steps:
step one, putting 1, 4-dichlorobutene and THF into a reactor in proportion, stirring and heating, dissolving methyl magnesium chloride in THF to form a THF solution, dropwise adding the THF solution into the reactor, controlling the temperature to react after dropwise adding, quenching and hydrolyzing with a saturated ammonium chloride solution when the content of 1, 4-dichlorobutene is less than 1%, adding water to dissolve salt, separating out an organic phase, recovering the solvent THF at normal pressure, and then carrying out reduced pressure rectification to obtain an intermediate product 1-chloro-2-pentene;
step two, putting 2, 5-hexanedione and dibromomethane in a certain proportion into a reactor, stirring, dropwise adding a sodium hydroxide solution, finishing dropping, heating, performing reflux reaction until the content of the 2, 5-hexanedione is less than 1%, cooling, neutralizing and washing, recovering solvent dibromomethane from a separated organic phase at normal pressure, and performing reduced pressure rectification to obtain an intermediate product, namely 3-methyl-2-cyclopentene-1-one;
and step three, putting the 1-chloro-2-pentene obtained in the step one and the 3-methyl-2-cyclopentene-1-ketone obtained in the step two into a reactor in proportion, adding ethanol and sodium hydroxide, stirring, controlling the temperature to react, recovering ethanol at normal pressure when the content of the 3-methyl-2-cyclopentene-1-ketone is less than 1 percent as a reaction end point, neutralizing and washing, and carrying out vacuum rectification on the organic phase to obtain a cis-jasmone finished product.
2. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the first step, the molar ratio of the 1, 4-dichlorobutene to the methyl magnesium chloride is 1: 1.1-1.3; 1, 4-dichlorobutene and THF are put into a reactor according to the mass ratio of 1: 3; the mass concentration of methyl magnesium chloride in the THF solution was 25%.
3. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the first step, the 1, 4-dichlorobutene is cis-1, 4-dichlorobutene.
4. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the first step, the temperature of the temperature control reaction is 20-25 ℃.
5. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the first step, the recovered solvent THF can be reused.
6. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the second step, the mass ratio of the 2, 5-hexanedione to the dibromomethane is 1: 3; the molar ratio of the 2, 5-hexanedione to the sodium hydroxide in the sodium hydroxide solution is 1: 1; the mass concentration of the sodium hydroxide is 10%.
7. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the second step, the recovered solvent dibromomethane can be reused.
8. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the third step, the molar ratio of the 1-chloro-2-pentene to the 3-methyl-2-cyclopenten-1-one is 1.1-1.3: 1; the mass ratio of the 3-methyl-2-cyclopentene-1-ketone to the ethanol is 1: 3; the mass ratio of the 3-methyl-2-cyclopentene-1-ketone to the sodium hydroxide is 1: 0.5.
9. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the third step, the temperature-controlled reaction temperature is 30-40 ℃.
10. The method of claim 1, wherein the step of synthesizing the cis-jasmone comprises the following steps: in the third step, the recovered solvent ethanol can be reused.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045489A (en) * | 1976-01-15 | 1977-08-30 | International Flavors & Fragrances Inc. | Process for producing cis-jasmone |
| CN105294418A (en) * | 2015-11-11 | 2016-02-03 | 中国科学院山西煤炭化学研究所 | Method for preparing 3-methyl-2-cyclopentene-1-ketone |
| CN112028757A (en) * | 2020-09-08 | 2020-12-04 | 乐威医药（江苏）股份有限公司 | Preparation method of 3-methyl-2-cyclopentene-1-ketone |
| CN112142582A (en) * | 2020-09-16 | 2020-12-29 | 上海应用技术大学 | Synthetic method of methyl cyclopentenolone |
-
2021
- 2021-12-16 CN CN202111541400.XA patent/CN114409519A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045489A (en) * | 1976-01-15 | 1977-08-30 | International Flavors & Fragrances Inc. | Process for producing cis-jasmone |
| CN105294418A (en) * | 2015-11-11 | 2016-02-03 | 中国科学院山西煤炭化学研究所 | Method for preparing 3-methyl-2-cyclopentene-1-ketone |
| CN112028757A (en) * | 2020-09-08 | 2020-12-04 | 乐威医药（江苏）股份有限公司 | Preparation method of 3-methyl-2-cyclopentene-1-ketone |
| CN112142582A (en) * | 2020-09-16 | 2020-12-29 | 上海应用技术大学 | Synthetic method of methyl cyclopentenolone |
Non-Patent Citations (1)
| Title |
|---|
| 官仕龙: "《基础有机化学习题精解》", vol. 1, 西南交通大学出版社, pages: 173 - 174 * |
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