Synthesis method of methyl dihydrojasmonate or intermediate thereof and catalyst used in synthesis method

A technology of methyl dihydrojasmonate and synthesis method, applied in the directions of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, preparation of carboxylate, etc., can solve the problem of unstable chemical and physical properties , The total yield of the final reaction is low, the reaction conditions are harsh, etc., to achieve the effect of great economic and environmental value, improve core competitiveness, and improve reaction safety

Pending Publication Date: 2022-04-15
SHANDONG NHU PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first oxidation reaction requires the use of noble metal catalysts ruthenium trichloride and expensive sodium periodate as catalysts, and the post-treatment process needs to be washed with hydrochloric acid and sodium thiosulfate, which cannot realize the recycling of expensive catalysts
Although the reaction rate of the esterification reaction catalyzed by thionyl chloride in the second step is relatively fast, the reaction conditions are relatively harsh and need to be carried out at a low temperature of -15°C
[0014] (1) The catalyst used in the Michael addition process cannot be recycled, the chemical and physical properties are extremely unstable, and there is a risk of explosion if i

Method used

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  • Synthesis method of methyl dihydrojasmonate or intermediate thereof and catalyst used in synthesis method
  • Synthesis method of methyl dihydrojasmonate or intermediate thereof and catalyst used in synthesis method
  • Synthesis method of methyl dihydrojasmonate or intermediate thereof and catalyst used in synthesis method

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Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0067] Preparation of Tetramethylammonium Hydroxide / Modified HY Catalyst

[0068] (1) Modification of HY molecular sieve

[0069] 450 g of HY-type molecular sieves were calcined in a muffle furnace at 800 °C under a nitrogen atmosphere for 8 hours, and then quickly cooled to room temperature by nitrogen purge cooling. Soak the calcined molecular sieve in 1.5 L of propylene glycol methyl ether acetate (PGMEA) solution, heat and stir at 150°C for 6 hours under nitrogen bubbling, filter and remove the propylene glycol methyl ether acetate at room temperature, and put the precursor A Heat and dry in an oven at 190° C. for 2 to 3 hours to obtain 460 g of modified HY type molecular sieve precursor A.

[0070] (2) Tetramethylammonium hydroxide supported by modified HY molecular sieve

[0071] Place the modified HY-type molecular sieve precursor A obtained in step (1) in 800 mL of methanol solution with a mass fraction of 15% tetramethylammonium hydroxide (TMAH, CAS: 10424-65-4), un...

Embodiment 2

[0081] Add 360g methyl acetate and 25g modified HY type molecular sieve supported tetrabutylammonium hydroxide quaternary ammonium base catalyst (loading capacity 15%) in the three-necked reaction flask with magnetic stirring, slowly add 401g dropwise in reaction system under 18 ℃ 2-pentylcyclopentenone, the dropwise addition time is 1.5h, and after the dropwise addition, continue to keep warm at 20°C for 3h. When the content of 2-pentylcyclopentenone is detected by gas phase ≤ 2%, the catalyst is recovered by filtration, 156g of methyl acetate is recovered under normal pressure, and 2.0g of residual 2-pentyl is recovered by distillation under reduced pressure (100-200pa) at 80-110°C After cyclopentenone, the crude product methyl dihydrojasmonate was obtained. Crude product obtains the qualified finished product 518g that content is 98.5% through 150~180 ℃, 100pa negative pressure rectification, and the molar yield of target product dihydrojasmonate methyl ester is 86.0% (with...

Embodiment 3～18

[0083] Change the kind of catalyst, according to the condition of embodiment 2, insulation reaction, after reaction finishes, carry out aftertreatment, calculate the yield of methyl dihydrojasmonate. The results are shown in the table below.

[0084] Table 2 Reaction yields of different catalyst types under the same reaction conditions

[0085]

[0086]

[0087]

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Abstract

The invention discloses a synthetic method of methyl dihydrojasmonate or an intermediate thereof, which comprises the following steps: under the action of a supported catalyst, carrying out Michael addition reaction on 2-pentylcyclopentenone and methyl acetate or dimethyl malonate to obtain the methyl dihydrojasmonate or the intermediate thereof, the supported catalyst comprises a carrier and an active component supported on the carrier; the active component is quaternary ammonium base, and the carrier is a modified molecular sieve; the modified molecular sieve is obtained by modifying a molecular sieve with propylene glycol methyl ether acetate. According to the synthesis method, a super-strong base or strong base catalyst which is extremely unstable and has harsh reaction conditions in the prior art is replaced, reaction steps are reduced, the reaction conditions tend to be mild, and the reaction safety is improved. The invention further discloses a catalyst used in the synthesis method.

Description

technical field [0001] The invention belongs to the technical field of perfume synthesis, and relates to a method for synthesizing methyl dihydrojasmonate or an intermediate thereof and a used catalyst. Background technique [0002] Methyl Dihydrojasmonate (MDJ for short) is a newly synthesized jasmone-like compound and is a very important spice in the modern perfume industry. The chemical properties are relatively stable, and it is not easy to change color when placed at room temperature. Its unique jasmine fragrance has become the first choice for perfumers to prepare fragrances. It is often used in the preparation of jasmine, lily of the valley, tuberose and oriental flavors. The introduction of the methyl dihydrojasmonate can produce an elegant and lifelike natural floral fragrance in the essence and fragrance, and the fragrance can be used not only for flavoring but also for processing and application of food fragrance. Because of its mild fragrance and long lasting fr...

Claims

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Application Information

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IPC IPC(8): C07C69/716C07C67/343B01J31/02
Inventor 方万军马啸刘本根于明徐田龙宁宇峰马世民任顺
Owner SHANDONG NHU PHARMA
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