New method for synthesizing raspberry ketone by using natural equivalent anisic aldehyde

A technology of raspberry ketone and anisaldehyde, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve the problems of consumption and environmental protection, and achieve low energy consumption and synthetic process route Innovation, the effect of short lines

Active Publication Date: 2010-06-02
GUANGXI WANSHAN SPICE
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  • Claims
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Problems solved by technology

This process requires the use of more toxic alkylamines (such as n-butylamine), and also consumes aluminum trichloride and a large amount of

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  • New method for synthesizing raspberry ketone by using natural equivalent anisic aldehyde
  • New method for synthesizing raspberry ketone by using natural equivalent anisic aldehyde
  • New method for synthesizing raspberry ketone by using natural equivalent anisic aldehyde

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Embodiment Construction

[0016] 1. Preparation of 4-(4-methoxyphenyl)-3-buten-2-one from natural equivalent anisaldehyde:

[0017] Natural equivalent anisaldehyde is raw material (28.4g, 0.2086mol), add water (30ml), sodium hydroxide (8.0g), acetone (30ml), reaction temperature is between 20-40 ℃, react for 5.5 hours, separate The oil phase was dried overnight with anhydrous magnesium sulfate; the solvent was removed by rotary evaporation to obtain the (Claisen-Schmidt) condensation product: 4-(4-methoxyphenyl)-3-buten-2-one.

[0018] 2. Preparation of anisyl acetone by catalytic hydrogenation reduction:

[0019] The product 4-(4-p-methoxyphenyl)-3-buten-2-one is dissolved in ethanol, palladium carbon is added for catalysis, hydrogen is passed into the reaction solution and the hydrogen pressure is kept between 0-0.1MPa, React at 20-40°C (room temperature) for 2 hours, then recover ethanol and distill to obtain anisyl acetone. The weight ratio of each component is: 4-(4-methoxyphenyl)-3-buten-2-one:...

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Abstract

The invention belongs to the technical field of spices and fine chemical engineering, mainly relating to a new method for synthesizing raspberry ketone by using natural equivalent anisic aldehyde. The new method is characterized in that anisyl acetone is prepared by carrying out processes of Claisen-Schnidt condensation, hydrogenation reduction and the like on the natural equivalent anisic aldehyde, and the raspberry ketone is prepared by carrying out the processes of demethylation, subsequent crystallization, recrystallization and the like on the anisyl acetone at 50-80 DEG C. In the invention, the raspberry ketone can be prepared form the natural equivalent anisic aldehyde by three steps of process, and the new method has the advantages of simple, convenient and easily applied processes, moderate processing conditions, 67.5 percent of reaction yield, and capability of over 30-time cycle use of a hydrogenation catalyst. In addition, by adopting analysis methods of infra-redspectrum, nuclear magnetic resonance, mass spectrum and the like to represent the structure of a synthetic product, products of the invention have better and long-lasting faint scent compared with other synthesized type raspberry ketone.

Description

technical field [0001] The invention belongs to the technical field of spices and fine chemicals, and the main technical content is a new method for synthesizing raspberry ketone from natural equivalent anisaldehyde. Background technique [0002] The natural equivalent anisaldehyde is the anise aldehyde synthesized from the star anise oil extracted from the fruit and leaves of the natural plant star anise tree or the oxidation of anethole. [0003] Raspberry ketone (chemical name: p-hydroxybutyrophenone, English name: Raspberry Ketone, CAS number: 5471-51-2), is the main aroma component in natural raspberry fruit, and is a kind of ketone with elegant fruity fragrance. spices. [0004] Raspberry ketone is an excellent fixative because it can retain the aroma for a long time. It can be used as a fixative for fruity flavors in food flavoring, and is widely used in fruity flavors, especially strawberry, Among the essences of raspberry, jasmine, mastflower, tuberose, pineapple,...

Claims

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Application Information

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IPC IPC(8): C07C49/245C07C45/64C07C45/62C07C45/74
CPCY02P20/584
Inventor 杨少凡刘新伟黄徽
Owner GUANGXI WANSHAN SPICE
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