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Preparation method of 2,5-dimethyl-4-hydroxyl-3(2H)furanone

A technology of diacetylfuran and diacetoxyfuran, which is applied in the field of preparation of 2,5-dimethyl-4-hydroxy-3-furanone, can solve the problems of lack of green chemical process and achieve synthesis operation and purification The effect of simplicity, high yield, and short synthetic route

Pending Publication Date: 2019-05-31
方国华
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above methods all lack the characteristics of green chemical process

Method used

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  • Preparation method of 2,5-dimethyl-4-hydroxyl-3(2H)furanone
  • Preparation method of 2,5-dimethyl-4-hydroxyl-3(2H)furanone
  • Preparation method of 2,5-dimethyl-4-hydroxyl-3(2H)furanone

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Embodiment 1

[0037] The preparation method of the present embodiment 2,5-dimethyl-3,4-diacetylfuran is as follows:

[0038] (1) Preparation of 2,5-dimethyl-3,4-diacetylfuran

[0039]The reaction device is: a 2000ml four-neck round bottom flask equipped with a thermometer, a mechanical stirrer, a water separator, a condenser tube and a silicone oil bath. The four-necked round-bottomed flask is placed in a silicone oil bath, and the thermometer and the water separator are installed on the four-necked round-bottomed flask, and the condenser tube is installed on the upper end of the water separator, and 198g of 3, 4-Diacetyl-2,5-hexanedione, 1000ml of xylene and 6.8g of potassium hydrogensulfate, start the stirrer to stir, heat up the silicone oil bath and reflux to separate the water, stop heating until no water comes out, cool to room temperature, filter The catalyst was removed, and the solvent was removed from the filtrate by distillation under reduced pressure to obtain 190.7 g of crude ...

Embodiment 2

[0045] The preparation method of the present embodiment 2,5-dimethyl-3,4-diacetylfuran is as follows:

[0046] (1) Preparation of 2,5-dimethyl-3,4-diacetylfuran

[0047] The reaction device is: a 2000ml four-neck round bottom flask equipped with a thermometer, a mechanical stirrer, a water separator, a condenser tube and a silicone oil bath. Place the four-necked round-bottomed flask in a silicone oil bath, install the thermometer and the water separator on the four-necked round-bottomed flask, and install the condenser tube on the upper end of the water separator, add 198g of 3, 4-Diacetyl-2,5-hexanedione, 1000ml of toluene and 15g of solid sulfonic acid (high-temperature type, produced by Kairui Environmental Technology Co., Ltd.), start stirring, raise the temperature and reflux to separate water until almost no water comes out and stop heating , cooled to room temperature, filtered off the catalyst solid sulfonic acid, and the filtrate was distilled under reduced pressure...

Embodiment 3

[0053] The preparation method of the present embodiment 2,5-dimethyl-3,4-diacetylfuran is as follows:

[0054] (1) Preparation of 2,5-dimethyl-3,4-diacetylfuran

[0055] The reaction device is: a 2000ml four-neck round bottom flask equipped with a thermometer, a mechanical stirrer, a water separator, a condenser tube and a silicone oil bath. The four-necked round-bottomed flask is placed in a silicone oil bath, and the thermometer and the water separator are installed on the four-necked round-bottomed flask, and the condenser tube is installed on the upper end of the water separator, and 198g of 3, 4-Diacetyl-2,5-hexanedione, 1000ml of xylene and 10.8g of solid phosphonic acid, start the stirrer to stir, heat up the silicone oil bath and reflux to separate water, stop heating until no water comes out, cool to room temperature, filter The catalyst was removed, and the solvent was removed from the filtrate by distillation under reduced pressure to obtain 188.6 g of crude 2,5-di...

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Abstract

The invention discloses a preparation method of 2,5-dimethyl-4-hydroxyl-3(2H)furanone. The preparation method comprises following three steps: (1) taking an easily available 3,4-diacetyl-2,5-hexanedione as the primary raw material, and carrying out intra-molecular dehydration to close the ring to obtain 2,5-dimethyl-3,4-diacetyl furan in the presence of a catalyst; (2) oxidizing 2,5-dimethyl-3,4-diacetyl furan through Baeyer-Villiger oxidation to obtain 2,5-dimethyl-3,4-diacetoxyl furan; and (3) hydrolyzing 2,5-dimethyl-3,4-diacetoxyl furan to obtain 2,5-dimethyl-4-hydroxyl-3(2H)furanone. Theused raw material 3,4-diacetyl-2,5-hexanedione is prepared through coupling or electrochemical coupling of acetyl acetone under the action of NBS and an alkali; the raw material preparation is simple, the raw material is easily available, at the same time, the synthesis route is short, the yield is high, the synthesis conditions are mild, the operation is simple, the purification method is simple, the yield is high, no toxic gas such as hydrogen bromide is generated, and the generated wastewater, waste solids, and waste gas are little.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of 2,5-dimethyl-4-hydroxy-3(2H)furanone. Background technique [0002] 2,5-Dimethyl-4-hydroxy-3(2H)furanone has a strong caramel aroma, and also has a strong fruit aroma and jam flavor. After dilution, it has a raspberry aroma. Its aroma characteristics are similar to maltol, but Coke gas is heavier than maltol. 2,5-Dimethyl-4-hydroxy-3(2H)furanone has an extremely low aroma threshold (0.04ppb), and a small amount of addition has obvious aroma-enhancing and modifying effects, and the aroma is long-lasting. It is an important raw material for sweet flavors And an excellent flavor enhancer, it is a safe food flavor jointly approved by the American Food Flavor Manufacturers Association (FEMA No.3174) and the Council of Europe (COE No.536). There are many synthetic methods of 2,5-dimethyl-4-hydroxy-3(2H)furanone reported in the literature,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60
Inventor 方国华
Owner 方国华
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