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CN114409519B - Synthesis method of cis-jasmone - Google Patents

Synthesis method of cis-jasmone Download PDF

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CN114409519B
CN114409519B CN202111541400.XA CN202111541400A CN114409519B CN 114409519 B CN114409519 B CN 114409519B CN 202111541400 A CN202111541400 A CN 202111541400A CN 114409519 B CN114409519 B CN 114409519B
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CN114409519A (en
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陈文抗
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Jiangsu Hongbang Chemical Technology Co ltd
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    • 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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    • 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
    • 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
    • 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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    • 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
    • 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

本发明公开了一种顺式茉莉酮的合成方法，具体包括以下步骤：1,4‑二氯丁烯与甲基氯化镁在THF介质中进行格氏反应，得到1‑氯‑2‑戊烯。2,5‑己二酮在二溴甲烷介质中及强碱性条件下进行环合反应，得到3‑甲基‑2‑环戊烯‑1‑酮。1‑氯‑2‑戊烯与3‑甲基‑2‑环戊烯‑1‑酮在乙醇介质中及碱性条件下进行加成/消除反应，得到顺式茉莉酮。本发明与其它合成方法相比，具有工艺路线短、反应选择性和转化率高、产品收率高、成本低等优点。The invention discloses a method for synthesizing cis-jasmone, which specifically comprises the following steps: 1,4-dichlorobutene and methylmagnesium chloride are subjected to a Grignard reaction in a THF medium to obtain 1-chloro-2-pentene. 2,5-hexanedione is subjected to a cyclization reaction in a dibromomethane medium under a strongly alkaline condition to obtain 3-methyl-2-cyclopentene-1-one. 1-chloro-2-pentene and 3-methyl-2-cyclopentene-1-one are subjected to an addition/elimination reaction in an ethanol medium under an alkaline condition to obtain cis-jasmone. Compared with other synthetic methods, the present invention has the advantages of a short process route, high reaction selectivity and conversion rate, high product yield, low cost, and the like.

Description

Synthesis method of cis-jasmone
Technical Field
The invention belongs to the technical field of organic synthesis, relates to synthesis of perfume, and in particular relates to a synthesis method of cis-jasmone.
Background
Cis-jasmone, the academic name of 3-methyl-2- (2-pentene) -2-cyclopenten-1-one, is colorless to pale yellow oily liquid, is slightly soluble in water, and can be dissolved in ethanol, diethyl ether and carbon tetrachloride. Cis-jasmone naturally exists in jasmine, peppermint, pepper, spearmint, jonquil, bergamot and tea, and has good diffusibility of floral fragrance and elegant jasmine fragrance. The jasmine essence is mainly used as a perfume base of jasmine perfumes and is widely applied to jasmine-flavored daily chemical essence, and various edible essences such as jasmine tea, strawberry, pineapple, peppermint-flavored edible essence and the like.
Various synthesis methods of cis-jasmone are reported, such as 1, cyclopentene-2-ketone is used as raw material, beta-sulphonation is carried out with sodium benzene sulphinate to obtain 3-sulfonyl cyclopentanone, then condensation is carried out with ethylene glycol under acidic condition to obtain ketal, beta-side chain alkenyl is carried out, and after acidification treatment, aldol condensation is carried out to obtain cis-jasmone. 2. 2-methylfuran is used as a raw material, firstly, 3- (2-methyl-5-furyl) propanal is condensed with acrolein under alkaline conditions, then 2-methyl-5- (3-hexenyl) furan is generated through Wittig reaction, undecylenic diketone is prepared through ring opening under acidic conditions, and finally cis-jasmone is obtained through ring closing by condensation under alkaline conditions. 3. Taking furfural as a raw material, firstly carrying out 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 to cis-2-pentenyl-2-cyclopentenone under an acidic condition, and finally carrying out methylation reaction with methyl iodide to obtain cis-jasmone. The methods have the problems of longer synthetic process route, lower product yield, large three wastes, difficult treatment and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a synthesis method of 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 synthesis method of cis-jasmone, comprising the following steps:
Firstly, 1, 4-dichlorobutene and THF are put into a reactor according to a proportion, stirring and heating are carried out, methyl magnesium chloride is dissolved in THF to form THF solution and is dripped into the reactor, temperature control reaction is carried out after dripping is finished, when the content of 1, 4-dichlorobutene is less than 1% as a reaction end point, saturated ammonium chloride solution is used for quenching and hydrolyzing, water is added for dissolving salt, an organic phase is separated, solvent THF is recovered under normal pressure, and then decompression rectification is carried out to obtain an intermediate product 1-chloro-2-pentene;
Step two, adding 2, 5-hexanedione and dibromomethane in a certain proportion into a reactor, stirring, dropwise adding sodium hydroxide solution, heating and refluxing until the content of 2, 5-hexanedione is less than 1% as a reaction end point, cooling, neutralizing and washing, recovering the solvent dibromomethane from the separated organic phase at normal pressure, and performing reduced pressure rectification to obtain an intermediate product 3-methyl-2-cyclopentene-1-one;
And thirdly, putting the 1-chloro-2-pentene obtained in the first step and the 3-methyl-2-cyclopentene-1-one obtained in the second step into a reactor according to a proportion, adding ethanol and sodium hydroxide, stirring, controlling the temperature for reaction, and when the content of the 3-methyl-2-cyclopentene-1-one is less than 1% as a reaction end point, recovering the ethanol at normal pressure, neutralizing and washing, and rectifying an organic phase under reduced pressure 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 mol ratio of the 1, 4-dichloro butene to the methyl magnesium chloride is 1:1.1-1.3, the 1, 4-dichloro butene and the THF are put into a reactor according to the mass ratio of 1:3, and the mass concentration of the methyl magnesium chloride in the THF solution is 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 ℃ to 25 ℃.
Further, in the first step, the recovered solvent THF can be reused.
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 sodium hydroxide in the sodium hydroxide solution is 1:1, and 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-cyclopenten-1-one to the ethanol is 1:3, and the mass ratio of the 3-methyl-2-cyclopenten-1-one 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 beneficial effects of the invention are as follows:
Compared with other synthetic 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 (1 mol) of 1, 4-dichlorobutene and 375g of THF are put into a reactor, stirred and heated to 20 ℃, 328g (1.1 mol) of methyl magnesium chloride (25% THF solution) is slowly added dropwise, the temperature is controlled to 20-25 ℃ after the dropwise addition, and the reaction is stirred and carried out, when the content of the 1, 4-dichlorobutene is less than 1%, the reaction is ended. Adding saturated ammonium chloride solution to quench and hydrolyze, adding water to dissolve salt, separating out organic phase, recovering solvent THF (repeatedly used) at normal pressure, and rectifying under reduced pressure to obtain intermediate product 1-chloro-2-pentene. The effective dose of the product is 91g, and the yield is 87.1%.
57G (0.5 mol) of 2, 5-hexanedione and 171g of dibromomethane are put into a reactor, 200g (0.5 mol) of 10% sodium hydroxide solution is added dropwise under stirring, and the temperature-rising reflux reaction is completed until the content of the 2, 5-hexanedione is less than 1% as the end point of the reaction. Cooling, neutralizing and washing, recovering solvent dibromomethane (reused) from separated organic phase at normal pressure, and vacuum rectifying to obtain intermediate 3-methyl-2-cyclopenten-1-one. The effective dose of the product is 87g, and the yield is 90.6%.
115G (1.1 mol) of intermediate product 1-chloro-2-pentene, 96g (1 mol) of intermediate product 3-methyl-2-cyclopentene-1-ketone, 288g of ethanol and 48g of sodium hydroxide are sequentially added into the reactor, stirred and heated, the temperature is controlled to be 30-40 ℃ for reaction, and when the content of 3-methyl-2-cyclopentene-1-ketone is less than 1%, the reaction is ended. The ethanol is recovered at normal pressure (reused), then the ethanol is neutralized and washed, and the organic phase is decompressed and rectified to obtain the cis-jasmone finished product. The effective amount of the product is 129g, and the yield is 78.7%.
Example 2
125G (1 mol) of 1, 4-dichlorobutene and 375g of THF are put into a reactor, stirred and heated to 20 ℃, 358g (1.2 mol) of methyl magnesium chloride (25% THF solution) is slowly added dropwise, the temperature is controlled to 20-25 ℃ after the dropwise addition, and the reaction is stirred and carried out, when the content of the 1, 4-dichlorobutene is less than 1%, the reaction is ended. Adding saturated ammonium chloride solution to quench and hydrolyze, adding water to dissolve salt, separating out organic phase, recovering solvent THF (repeatedly used) at normal pressure, and rectifying under reduced pressure to obtain intermediate product 1-chloro-2-pentene. The effective dose of the product is 95g, and the yield is 90.9%.
114G (1 mol) of 2, 5-hexanedione and 342g of dibromomethane are put into a reactor, and 400g (1 mol) of 10% sodium hydroxide solution is added dropwise under stirring, and the temperature-rising reflux reaction is completed until the content of the 2, 5-hexanedione is less than 1% as the end point of the reaction. Cooling, neutralizing and washing, recovering solvent dibromomethane (reused) from separated organic phase at normal pressure, and vacuum rectifying to obtain intermediate 3-methyl-2-cyclopenten-1-one. The effective amount of the product is 88g, and the yield is 91.7%.
125G (1.2 mol) of intermediate product 1-chloro-2-pentene, 96g (1 mol) of intermediate product 3-methyl-2-cyclopentene-1-ketone, 288g of ethanol and 48g of sodium hydroxide are sequentially added into the reactor, stirred and heated, the temperature is controlled to be 30-40 ℃ for reaction, and when the content of 3-methyl-2-cyclopentene-1-ketone is less than 1%, the reaction is ended. The ethanol is recovered at normal pressure (reused), then the ethanol is neutralized and washed, and the organic phase is decompressed and rectified to obtain the cis-jasmone finished product. The effective dose of the product is 132g, and the yield is 80.5%.
Example 3
125G (1 mol) of 1, 4-dichlorobutene and 375g of THF are put into a reactor, stirred and heated to 20 ℃, 388g (1.3 mol) of methyl magnesium chloride (25% THF solution) is slowly added dropwise, the temperature is controlled to 20-25 ℃ after the dropwise addition, and the reaction is stirred and carried out, when the content of 1, 4-dichlorobutene is less than 1%, the reaction is ended. Adding saturated ammonium chloride solution to quench and hydrolyze, adding water to dissolve salt, separating out organic phase, recovering solvent THF (repeatedly used) at normal pressure, and rectifying under reduced pressure to obtain intermediate product 1-chloro-2-pentene. The effective dose of the product is 92g, and the yield is 88.1%.
171G (1.5 mol) of 2, 5-hexanedione and 513g of dibromomethane are put into a reactor, and 600g (1.5 mol) of 10% sodium hydroxide solution is added dropwise under stirring, and the temperature-rising reflux reaction is completed until the content of the 2, 5-hexanedione is less than 1% as the end point of the reaction. Cooling, neutralizing and washing, recovering solvent dibromomethane (reused) from separated organic phase at normal pressure, and vacuum rectifying to obtain intermediate 3-methyl-2-cyclopenten-1-one. The effective amount of the product is 86g, and the yield is 89.6%.
136G (1.3 mol) of intermediate product 1-chloro-2-pentene, 96g (1 mol) of intermediate product 3-methyl-2-cyclopentene-1-ketone, 288g of ethanol and 48g of sodium hydroxide are sequentially added into the reactor, stirred and heated, the temperature is controlled to be 30-40 ℃ for reaction, and when the content of 3-methyl-2-cyclopentene-1-ketone is less than 1%, the reaction is ended. The ethanol is recovered at normal pressure (reused), then the ethanol is neutralized and washed, and the organic phase is decompressed and rectified to obtain the cis-jasmone finished product. The effective dose of the product is 128g, and the yield is 78.1%.

Claims (6)

1.一种顺式茉莉酮的合成方法，其特征在于，包括以下步骤：1. A method for synthesizing cis-jasmone, characterized in that it comprises the following steps: 步骤一，将1,4-二氯丁烯、THF按比例投入反应器中，搅拌升温，将甲基氯化镁溶于THF形成THF溶液并滴加至反应器，滴完后控温反应，当1,4-二氯丁烯含量小于1%为反应终点，用饱和氯化铵溶液淬灭水解，再加入水溶解盐，分离出有机相，先常压回收溶剂THF，再减压精馏得中间产品1-氯-2-戊烯；Step 1: Add 1,4-dichlorobutene and THF into a reactor in proportion, stir and heat, dissolve methylmagnesium chloride in THF to form a THF solution and add it dropwise to the reactor, control the temperature and react after the addition is complete, when the content of 1,4-dichlorobutene is less than 1%, the reaction is terminated, quench and hydrolyze with a saturated ammonium chloride solution, add water to dissolve the salt, separate the organic phase, first recover the solvent THF at normal pressure, and then perform vacuum distillation to obtain the intermediate product 1-chloro-2-pentene; 步骤二，反应器中投入一定比例的2,5-己二酮和二溴甲烷，搅拌，滴加氢氧化钠溶液，滴完升温回流反应，至2,5-己二酮含量小于1%为反应终点，冷却，中和洗涤，分出的有机相先常压回收溶剂二溴甲烷，再减压精馏得中间产品3-甲基-2-环戊烯-1-酮；Step 2: Add a certain proportion of 2,5-hexanedione and dibromomethane into the reactor, stir, add sodium hydroxide solution dropwise, heat and reflux to react until the content of 2,5-hexanedione is less than 1% as the reaction end point, cool, neutralize and wash, and first recover the solvent dibromomethane from the separated organic phase under normal pressure, and then perform vacuum distillation to obtain the intermediate product 3-methyl-2-cyclopentene-1-one; 步骤三，将步骤一得到的1-氯-2-戊烯和步骤二得到的3-甲基-2-环戊烯-1-酮按比例投入反应器中，加入乙醇和氢氧化钠，搅拌，控温反应，当3-甲基-2-环戊烯-1-酮含量小于1%为反应终点，先常压回收乙醇，然后中和洗涤，有机相减压精馏得顺式茉莉酮成品；Step 3, the 1-chloro-2-pentene obtained in step 1 and the 3-methyl-2-cyclopentene-1-one obtained in step 2 are put into a reactor in proportion, ethanol and sodium hydroxide are added, stirred, and the temperature is controlled to react. When the content of 3-methyl-2-cyclopentene-1-one is less than 1%, the reaction end point is reached, ethanol is first recovered under normal pressure, then neutralized and washed, and the organic phase is subjected to vacuum distillation to obtain a cis-jasmone product; 步骤一中，所述1,4-二氯丁烯与甲基氯化镁的摩尔比为1:1.1~1.3；1,4-二氯丁烯与THF按质量比1:3投入反应器；THF溶液中甲基氯化镁的质量浓度为25%；所述控温反应的温度为20℃~25℃；In step 1, the molar ratio of 1,4-dichlorobutene to methylmagnesium chloride is 1:1.1-1.3; 1,4-dichlorobutene and THF are added to the reactor at a mass ratio of 1:3; the mass concentration of methylmagnesium chloride in the THF solution is 25%; the temperature of the temperature-controlled reaction is 20°C-25°C; 步骤三中，所述1-氯-2-戊烯与3-甲基-2-环戊烯-1-酮的摩尔比为1.1~1.3:1；所述3-甲基-2-环戊烯-1-酮与乙醇的质量比为1:3；所述3-甲基-2-环戊烯-1-酮与氢氧化钠的质量比为1:0.5；所述控温反应温度为30℃~40℃。In step three, the molar ratio of 1-chloro-2-pentene to 3-methyl-2-cyclopentene-1-one is 1.1-1.3:1; the mass ratio of 3-methyl-2-cyclopentene-1-one to ethanol is 1:3; the mass ratio of 3-methyl-2-cyclopentene-1-one to sodium hydroxide is 1:0.5; and the temperature control reaction temperature is 30°C-40°C. 2.根据权利要求1所述的一种顺式茉莉酮的合成方法，其特征在于：步骤一中，所述1,4-二氯丁烯为顺式1,4-二氯丁烯。2. The method for synthesizing cis-jasmone according to claim 1, characterized in that: in step 1, the 1,4-dichlorobutene is cis-1,4-dichlorobutene. 3.根据权利要求1所述的一种顺式茉莉酮的合成方法，其特征在于：步骤一中，回收的溶剂THF可重复使用。3. The method for synthesizing cis-jasmone according to claim 1, wherein in step 1, the recovered solvent THF can be reused. 4.根据权利要求1所述的一种顺式茉莉酮的合成方法，其特征在于：步骤二中，所述2,5-己二酮与二溴甲烷的质量比为1:3；所述2,5-己二酮与氢氧化钠溶液中氢氧化钠的摩尔比为1：1；所述氢氧化钠的质量浓度为10%。4. The method for synthesizing cis-jasmone according to claim 1, characterized in that: in step 2, the mass ratio of 2,5-hexanedione to dibromomethane is 1:3; the molar ratio of 2,5-hexanedione to sodium hydroxide in the sodium hydroxide solution is 1:1; and the mass concentration of the sodium hydroxide is 10%. 5.根据权利要求1所述的一种顺式茉莉酮的合成方法，其特征在于：步骤二中，回收的溶剂二溴甲烷可重复使用。5. The method for synthesizing cis-jasmone according to claim 1, characterized in that: in step 2, the recovered solvent dibromomethane can be reused. 6.根据权利要求1所述的一种顺式茉莉酮的合成方法，其特征在于：步骤三中，回收的溶剂乙醇可重复使用。6. The method for synthesizing cis-jasmone according to claim 1, characterized in that: in step 3, the recovered solvent ethanol can be reused.
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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

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