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Method for synthesizing beta-damascenone

A technology of tukelenone and tukelenone, which is applied in the field of synthesizing β-tekelenone, can solve problems such as high safety risks, and achieve the effects of simple process operation, low cost and mild reaction conditions

Active Publication Date: 2018-12-21
XIAMEN OMIC BIOTECH CO LTD
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Problems solved by technology

[0018] Metal sodium and liquid ammonia are used in the reaction of p reduction in this process, and the safety risk is relatively large

Method used

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  • Method for synthesizing beta-damascenone
  • Method for synthesizing beta-damascenone
  • Method for synthesizing beta-damascenone

Examples

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Embodiment Construction

[0047] Below by embodiment the content of the present invention is specified:

[0048] 1) Synthesis of α-ringgeranic acid:

[0049] Step 1: Using citral as a raw material, an intermediate of geranic acid is obtained through an improved Pinnick oxidation reaction. specifically:

[0050] Add citral (100g), dipentene (446g), and tert-butanol (486g) to a 5L three-necked bottle, add 902g of 16.8% sodium dihydrogen phosphate aqueous solution, and slowly add 20% of it dropwise at 15°C. Sodium chlorite solution 379.6g, the temperature is not higher than 35°C; after the dropwise addition, stir and react at room temperature for 16h; when the raw materials are completely reacted, separate the liquid, separate the upper organic phase, and extract the lower aqueous phase with toluene (2x100mL). The organic phases were combined, and tert-butanol and toluene were removed by rotary evaporation; then 400 g of 10% sodium hydroxide solution was stirred for 0.5 h, separated, the aqueous phase w...

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Abstract

The invention discloses a method for synthesizing beta-damascenone. The method mainly comprises the following steps: oxidizing citral through sodium chlorite; carrying out catalytic cyclization through concentrated phosphoric acid to obtain alpha-cyclogeranic acid; eliminating the alkalinity of the alpha-cyclogeranic acid under the action of thionyl chloride to obtain cyclogeranenone; carrying outaddition on the cyclogeranenone and allylmagnesium chloride and carrying out acidic isomerization to obtain alpha-damascenone; carrying out epoxidation on the alpha-damascenon through peroxyacetic acid, and carrying out alkaline ring opening through potassium carbonate; catalytically heating and dehydrating through para-toluenesulfonic acid to obtain the beta-damascenone. The method disclosed bythe invention has the advantages that raw materials are cheap and easy to obtain, reaction conditions are moderate and the operation is simple and convenient; another useful spice alpha-damascenone can be synchronously synthesized and the method is a method which is suitable for industrial production of the beta-damascenone.

Description

technical field [0001] The invention belongs to the technical field of fine chemical spices, and in particular relates to a method for synthesizing β-turkenone. During the synthesis process, the spice α-turkenone can also be produced synchronously. Background technique [0002] β-Damascenone (β-Damascenone), also known as β-Damascenone, chemical name 4-(2,6,6-trimethyl-1,3-cyclohexadiene)-2-butene -4-ketone, pale yellow to yellow liquid, CAS: 23696-85-7. Because of its seductive rose fragrance, raspberry-like fruity fragrance and diffusive power, it has become a precious fragrance raw material. This raw material was first discovered by Ohloff in Bulgarian Turkic rose oil in a small amount, and it is a key aroma component. In recent years, with the development of the perfume industry and the improvement of synthetic technology, its price has also been lowered, and its usage has also increased year by year. β-Turkelenone spices are not only used as precious fragrance raw ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/557C07C45/66
CPCC07C45/64C07C45/66C07C45/68C07C45/89C07C51/25C07C51/353C07D301/14C07D303/32C07C2601/16C07C57/03C07C61/22C07C49/88C07C49/557C07C49/573
Inventor 徐初培柯顺川朱洲张弓长
Owner XIAMEN OMIC BIOTECH CO LTD
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