Preparation method of 6,7-epoxy-gamma-ionone

A technology of ionone and epoxy, applied in the field of preparation of 6,7-epoxy-γ-ionone, can solve the problems of long reaction route, low yield, unfriendly environment, etc., and achieve short reaction time and high production efficiency The effect of low cost and low price

Pending Publication Date: 2022-02-08
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The raw materials used in the preparation method are easy to obtain, the preparation process is simple, the operation is convenient, the environment is friendly, the cost is low, it is suitable for industrial production, and the problems of being unfriendly to the environment, long reaction route and low yield are solved.

Method used

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  • Preparation method of 6,7-epoxy-gamma-ionone

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preparation example Construction

[0026] The object of the present invention is to provide a kind of preparation method of 6,7-epoxy-γ-ionone, comprising the following steps:

[0027] (1) reacting α-ionone and NaOH in a dioxane solvent to obtain a neutral reaction solution;

[0028] (2) post-processing the neutral reaction solution obtained in step (1) to obtain the crude product of 6,7-epoxy-γ-ionone;

[0029] (3) Purifying the crude 6,7-epoxy-γ-ionone obtained in step (2) to obtain pure 6,7-epoxy-γ-ionone.

[0030] In one embodiment of the present invention, in step (1), the NaOH is an aqueous NaOH solution with a mass percentage of 10-30%; preferably, the NaOH aqueous solution is 25% by mass.

[0031] In one embodiment of the present invention, in step (1), the feeding ratio of the α-ionone, NaOH aqueous solution and dioxane is 1mol: 1-4mol: 1-3L.

[0032] In one embodiment of the present invention, in step (1), the reaction temperature is 50° C., and the reaction time is 6 to 9 hours; after the reaction,...

Embodiment 1

[0048] This embodiment provides a preparation method of 6,7-epoxy-γ-ionone, comprising the following steps:

[0049] (1) At 50°C, a mixed solution consisting of 5.00 grams (99.80%, 25.99mmoL) of α-ionone, 10.40mL (25.99mmoL) and 25.99mL dioxane in 10% by mass percentage, After stirring and reacting for 6 hours, the obtained reaction solution was washed with 5% HCl aqueous solution by mass percentage, and the pH of the washing was neutralized;

[0050] (2) the step (1) pH washing to neutral reaction solution is extracted with ether, and the organic layer of gained is washed with anhydrous MgSO 4Dry and filter with filter paper the next day, and the obtained filtrate is evaporated and concentrated by a rotary evaporator to obtain 4.01 g of crude product of 6,7-epoxy-γ-ionone, which is detected by gas chromatography. The purity is 93.70%, and the yield is 69.45% %;

[0051] (3) The crude product of 6,7-epoxy-γ-ionone obtained in step (2) is separated with a silica gel column, a...

Embodiment 2

[0055] This embodiment provides a preparation method of 6,7-epoxy-γ-ionone, comprising the following steps:

[0056] (1) At 50°C, a mixed solution composed of 5.29 grams of α-ionone (99.80%, 27.50mmol), 8.32mL (55.00mmol) of NaOH aqueous solution (55.00mmol) and 30mL of dioxane with a mass percent content of 25%, was stirred After reacting for 6 hours, the obtained reaction solution was washed with 10% HCl aqueous solution by mass percentage, and the pH of the washing was neutralized;

[0057] (2) step (1) pH washing to neutral reaction solution is extracted with ether, and the organic layer of gained is washed with anhydrous MgSO 4 Dry and filter with filter paper the next day, and the obtained filtrate is evaporated and concentrated by a rotary evaporator to obtain 4.37g of crude product of 6,7-epoxy-γ-ionone, which is detected by gas chromatography and has a purity of 95.65%, and a yield of 73.08% %;

[0058] (3) The crude product of 6,7-epoxy-γ-ionone obtained in step (2...

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Abstract

The invention relates to the technical field of preparation of oxygen-containing monocyclic terpenoid spices, in particular to a preparation method of 6, 7-epoxy-gamma-ionone. The preparation method comprises the following steps: reacting alpha-ionone and a NaOH aqueous solution in dioxane, and after the reaction is finished, washing with a hydrochloric acid aqueous solution until the pH value is neutral to obtain a neutral reaction solution; then carrying out post-treatment on the neutral reaction solution to obtain a 6, 7-epoxy-gamma-ionone crude product; and finally, subjecting the 6, 7-epoxy-gamma-ionone crude product to purification treatment, and obtaining a 6, 7-epoxy-gamma-ionone pure product. The invention provides the preparation method of 6, 7-epoxy-gamma-ionone, which has the advantages of easily available raw materials, simple preparation process and convenience in operation; and 6, 7-epoxy-gamma-ionone prepared by the method is relatively low in production cost and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of preparation of oxygen-containing monocyclic terpene fragrances, in particular to a preparation method of 6,7-epoxy-γ-ionone. Background technique [0002] 6,7-Epoxy-γ-ionone, a colorless liquid, is a terpenoid compound, and at the same time, it is also an oxygen-containing monocyclic terpene spice. It is a very useful spice and pharmaceutical intermediate, and is also a tropical plant and fruit. important constituents. There are few reports on the preparation of this compound. [0003] In 2004, Woitiskia CB, Kozlovb YN, Mandellia D, et al. (Oxidations by the system "hydrogen peroxide–dinuclear manganese (IV) complex–carboxylic acid" [J]. Journal of Molecular Catalysis A: Chemical, 2004, 222(1-2 ): 103-119) take hydrogen peroxide as oxidant, and then use different metal complexes as catalysts to carry out epoxidation synthesis of double bonds, and the yield is between 55% and 70%. The disadvantage is th...

Claims

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Application Information

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IPC IPC(8): C07D303/32C07D301/02
CPCC07D303/32C07D301/02
Inventor 杨始刚张格格
Owner SHANGHAI INST OF TECH
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