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Watermelon ketone synthesizing process

A synthetic process, the technology of watermelon ketone, applied in the field of synthetic watermelon ketone, to achieve the effect of reducing production cost, low boiling point, and environmental protection

Inactive Publication Date: 2013-01-23
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a kind of technology of synthesizing watermelon ketone for the weak point of existing method for synthesizing watermelon ketone, has high yield, few by-products, moderate reaction temperature, characteristics such as solvent separation is easy, the key point of the present invention is Improvement of 2-methoxycarbonylmethoxy-4-methyl-phenoxy-methyl acetate synthesis process, so as to improve the yield of watermelon ketone

Method used

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  • Watermelon ketone synthesizing process
  • Watermelon ketone synthesizing process
  • Watermelon ketone synthesizing process

Examples

Experimental program
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Effect test

Embodiment 1

[0033] The concrete steps of a kind of synthesis technique of watermelon ketone are as follows:

[0034] (1) Williamson condensation reaction

[0035] Potassium iodide is used as a catalyst, and potassium iodide is first dissolved in anhydrous acetone solvent to prepare a potassium iodide catalyst solution. The potassium iodide catalyst solution was then placed in the dried reflux reaction vessel, heated to 90° C., and then methyl bromoacetate was added dropwise. After the dropwise addition, potassium carbonate and 4-methyl catechol were added in turn, and After completion, the Williamson condensation reaction was carried out by stirring and refluxing at a constant temperature of 90° C. for 5 h, and the Williamson condensation reaction suspension was prepared. Wherein: the quality of potassium iodide: the volume ratio of anhydrous acetone solvent is 1g: 20ml; the quality of 4-methylcatechol: the quality of potassium iodide: the quality of potassium carbonate: the volume ratio...

Embodiment 2

[0050] A kind of concrete steps of the synthesis technique of watermelon ketone, with embodiment 1, wherein:

[0051]In the (1) step, the heating temperature in the reflux reactor is 80°C, and the Williamson condensation reaction is carried out under stirring and refluxing at a constant temperature of 80°C for 5.5h, wherein: the mass of potassium iodide: the volume ratio of anhydrous acetone solvent is 1g: 25ml ; The mass of 4-methylcatechol: the mass of potassium iodide: the mass of potassium carbonate: the volume ratio of methyl bromoacetate is 1g: 1g: 4.27g: 2.53ml.

[0052] In step (2), rotary evaporation is performed at 45° C. to remove the anhydrous acetone solvent, and the collected evaporation residue is washed with a 5% sodium hydroxide solution until the pH value is 8.5. The washed mixture was extracted with 15 times the volume of dichloromethane. The collected lower dichloromethane solution was back-extracted with 15 times the volume of water. Anhydrous sodium sul...

Embodiment 3

[0054] A kind of concrete steps of the synthesis technique of watermelon ketone, with embodiment 1, wherein:

[0055] In the (1) step, the heating temperature in the reflux reactor is 70 ℃, and stirring and refluxing at 70 ℃ constant temperature carries out Williamson condensation reaction 6h, wherein: the quality of potassium iodide: the volume ratio of anhydrous acetone solvent is 1g: 30ml; The volume ratio of the mass of 4-methylcatechol: the mass of potassium iodide: the mass of potassium carbonate: methyl bromoacetate is 1 g: 1.3 g: 4.27 g: 2.53 ml.

[0056] In step (2), rotary evaporation is performed at 50° C. to remove the anhydrous acetone solvent, and the collected evaporation residue is washed with a 5% sodium hydroxide solution until the pH value is 9. The washed mixture was extracted with 20 times the volume of dichloromethane. The collected lower dichloromethane solution was back-extracted with 20 times the volume of water. Anhydrous sodium sulfate was added to...

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Abstract

The invention discloses a watermelon ketone synthesizing process, and belongs to the technical field of essence and spice synthesis. The watermelon ketone synthesizing process comprises the following steps of: performing replacement reaction on methyl bromoacetate and potassium iodide serving as a catalyst; performing Williamson condensation reaction and posttreatment; performing Dieckmann intramolecular condensation reaction and posttreatment; and finally performing drolysis and decarboxylation reaction and posttreatment to obtain the watermelon ketone product. The watermelon ketone synthesizing process has the characteristics of high yield, product purity of 99.5 percent, mild reaction temperature, simple separation process, low production cost, convenient promotion and application and the like. The watermelon ketone synthesizing process can be widely applied to producing watermelon ketone; and the watermelon ketone synthesized by the process can be widely used as an essence and spice for products such as medicines, foods, and washing chemicals.

Description

technical field [0001] The invention belongs to the technical field of flavor and fragrance synthesis, and in particular relates to a process for synthesizing watermelon ketone by using potassium iodide as a catalyst. Background technique [0002] Watermelon ketone not only has fresh, fruity, seaweed and other special fragrances, but also has no toxic and side effects, and is widely used in the fragrance of medicine, food, washing and other products. Therefore, watermelon ketone is a high value-added fine chemical. In recent years, the market demand has increased year by year, and the market prospect is broad. [0003] Existing watermelon ketone synthesis methods, such as "a novel synthetic route of benzodioxpinone congeners that can be assessed by qualitative olfactory methods" ("HELVETICA CHEMICA ACTA"), 2007, volume 90 ( "Synthesis of Benzodioxepinone Analogues via a Novel SyntheticRoute with Qualitative Olfactory Evaluation"), the method disclosed is: use 4-methylcatech...

Claims

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Application Information

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IPC IPC(8): C07D321/10
Inventor 董立春黄少建江寒梅徐玉婷张雅峥谭世语李文平吴纪周
Owner CHONGQING UNIV
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