Preparation method of cis-jasmone

A technology of cis-jasmone and alkenone, which is applied in the field of preparation of cis-jasmone, can solve the problems of complex operation process, high preparation cost, and difficult process, and achieve simple preparation process, low process difficulty and low preparation. Favorable effects for mass production applications

Inactive Publication Date: 2018-04-20
JIANGXI SUNWAY CHEM CO LTD
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  • Claims
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Problems solved by technology

[0005] Based on this, the purpose of the present invention is to solve the problems that the industrial preparation of ci

Method used

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  • Preparation method of cis-jasmone

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Experimental program
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Effect test

Embodiment 1

[0026] see figure 2 , a preparation method of cis-jasmone, the specific preparation process is as follows:

[0027] (1) Preparation of 3-alkoxy-1,2-pentadiene (allene ether): the first prefabricated base and 3-alkoxy-1-pentyne are carried out according to the molar ratio of 0.001~0.1:1.0 Mix and carry out isomerization reaction at a temperature of 40° C. to 100° C. After 2 to 10 hours of reaction, 3-alkoxy-1,2-pentadiene is obtained.

[0028] Wherein, the first prefabricated base can be potassium tert-butoxide or potassium popentoxide, and 3-alkoxy-1,2-pentadiene can be 3-methoxy-1,2-pentadiene, 3- Ethoxy-1,2-pentadiene, 3-n-propoxy-1,2-pentadiene, 3-n-butoxy-1,2-pentadiene or 3-isobutoxy-1 , Any one of 2-pentadiene. It should also be pointed out here that, for the above-mentioned first preset temperature, the preferred range is 50° C. to 80° C.; for the above-mentioned first preset time, the preferred range is 4-8 hours.

[0029] (2) Preparation of 3-methyl-2-(2-pentynyl...

Embodiment 2

[0035] 1, Preparation of 3-methoxyl-1,2-pentadiene

[0036] In a 1000ml three-necked round-bottomed flask with a thermometer and a reflux condenser, add 687g of 3-methoxy-1-pentyne and 7.9g of potassium tert-butoxide, heat to 80°C, stir for 8 hours and then carry out normal pressure After distillation, 666 g of fractions at 110° C. to 112° C. were collected, corresponding to a yield of 97%.

[0037] 2. Preparation of 3-methyl-2-(2-pentynyl)-cyclopent-2-enone

[0038]In a 2000ml three-necked round bottom flask with a thermometer and a reflux condenser, add 192g of 3-methylcyclopent-2-enone, 255g of 3-methoxy-1,2-pentadiene, and 890g of tetrahydrofuran And 2.3g of 1,4-diazabicyclo[2.2.2]octane (DABCO), heated to reflux for 8h, cooled to room temperature, added 2.5g of benzoic acid, stirred at room temperature for 1h and then filtered, the filtrate first Recover tetrahydrofuran under normal pressure, then distill under reduced pressure, collect 107~110 ℃ / 1mmHg fraction, obtain ...

Embodiment 3

[0045] 1, Preparation of 3-methoxyl-1,2-pentadiene

[0046] In a 1000ml three-necked round bottom flask with a thermometer and a reflux condenser, add 687g of 3-methoxy-1-pentyne and 7.9g of potassium tert-butoxide, heat to 80°C, stir for 8 hours, and distill at atmospheric pressure , Collected 666g of fractions at 110-112°C, corresponding to a yield of 97%.

[0047] 2. Preparation of 3-methyl-2-(2-pentynyl)-cyclopent-2-enone

[0048] In a 2000ml three-neck round bottom flask with a thermometer and a reflux condenser, add 192g of 3-methylcyclopent-2-enone, 255g of 3-methoxy-1,2-pentadiene, and 890g of tetrahydrofuran And 4.0g of tri-n-butylphosphine, replace the air in the bottle with nitrogen three times, and heat to reflux for 8h. First recover tetrahydrofuran under normal pressure, then carry out vacuum distillation, collect 107~110 ℃ / 1mmHg fraction, obtain 282.3g of 3-methyl-2-(2-pentynyl)-cyclopent-2-enone, and collect The rate is 87%.

[0049] 3. Preparation of 3-met...

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Abstract

The invention relates to a preparation method of cis-jasmone. The preparation method of the cis-jasmone comprises the following steps: mixing a first prefabricated alkali with 3-alkoxy-1-pentyne, andallowing the mixture to react at a first preset temperature for a first predetermined time, so as to obtain 3-alkoxy-1,2-pentadiene; mixing the 3-alkoxy-1,2-pentadiene, 3-methylcyclopent-2-enone and afirst catalyst, and allowing the mixture to react at a second preset temperature for a second predetermined time, so as to obtain 3-methyl-2-(2-pentynyl)-cyclopent-2-enone; and adding the 3-methyl-2-(2-pentynyl)-cyclopent-2-enone and a first solvent into a hydrogenation reaction flask, and then adding a second catalyst into the hydrogenation reaction flask, performing gas-exchanging treatment onthe hydrogenation reaction flask, and allowing the mixture to react at a third preset temperature for a third predetermined time, so as to obtain the cis-jasmone. According to the preparation method of the cis-jasmone, the preparation process is simpler, and the process difficulty and preparation difficulty are low, so that large-scale production and application are facilitated.

Description

technical field [0001] The invention relates to the technical field of chemical raw material synthesis, in particular to a preparation method of cis-jasmone. Background technique [0002] Cis-jasmone is an important spice widely used. Its aroma is like jasmine. It is one of the important aroma components of jasmine oil. It is mainly used in high-grade jasmine series cosmetic essences. Its corresponding molecular formula is C 11 h 16 O. [0003] At present, there have been many reports on the synthesis of cis-jasmone, but most of them are only in the laboratory synthesis stage, and few of them can really be used in industrial production. Generally, in industrial production, the more commonly used method at home and abroad at present comprises the following steps: (1) 2-methylfuran and acrolein are reacted to obtain 3-(5-methyl-2-furyl) propionaldehyde; ( 2) 1-bromopropane reacts with triphenylphosphine to obtain n-propyltriphenylphosphonium bromide; (3) reacts n-propyltrip...

Claims

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Application Information

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IPC IPC(8): C07C41/32C07C43/15C07C45/68C07C49/597C07C45/62
CPCC07B2200/09C07C41/32C07C45/62C07C45/673C07C45/68C07C43/15C07C49/597
Inventor 汤恩江方国华
Owner JIANGXI SUNWAY CHEM CO LTD
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