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Magnolol synthesizing method

A synthesis method and magnolol technology are applied in the field of magnolol synthesis, which can solve the problems of low magnolol yield, harsh synthesis conditions, and no industrial applicability, and achieve high yield, simple synthesis process, and low cost. cost effect

Inactive Publication Date: 2011-09-28
JIANGNAN UNIV
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  • Claims
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Problems solved by technology

In accompanying drawing 6 of this patent specification, accompanying drawing 7 and specification page 7-8, have explained two kinds of synthetic methods of magnolol in addition, the main shortcoming that the method shown in accompanying drawing 6 exists is that the yield of magnolol is too high. Low, the main disadvantage of the method shown in Figure 7 is that the manufacturing process is long, and it must be synthesized under conditions of anhydrous, oxygen avoidance and low temperature, the synthesis conditions are harsh, and the cost is high
Therefore above-mentioned two kinds of methods all have no industrial applicability

Method used

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specific Embodiment approach

[0022] (one), figure 1 It is the synthesis route diagram of the embodiment of the present invention, such as figure 1 As shown, the whole synthesis is divided into three steps:

[0023] The first step prepares p-bromobenzyloxymethyl ether: p-bromophenol is dissolved in an acetone solvent, potassium carbonate and chloromethyl methyl ether (MOMCl) are added, and p-bromobenzyloxymethyl ether is obtained through reflux reaction;

[0024] The effect of the above reaction is to protect the hydroxyl group of p-bromophenol first, so that the hydroxyl group is not affected by the Grignard reaction described below. The expression of its reaction is as follows:

[0025]

[0026] The second step is to prepare p-allyl phenol: the p-bromobenzyloxymethyl ether prepared in the first step is reacted with allyl bromide under the participation of tetrahydrofuran solvent and magnesium chips to obtain p- Allylphenol; the expression for its reaction is as follows:

[0027]

[0028] The th...

Embodiment 1

[0037] Embodiment 1: the embodiment that the present invention synthesizes three steps, press figure 1 The synthetic route shown.

[0038] First prepare intermediate product p-allyl phenol, comprise following two steps:

[0039] Step A, prepare p-bromophenoxymethyl ether: put 25g (0.1445mol) p-bromophenol in a flask, add 200 ml acetone, dissolve p-bromophenol in acetone, then add 17.5g (0.127mol) carbonic acid Potassium, after stirring for 15 minutes, add 15g (0.185mol) chloromethyl methyl ether uniformly dropwise within about 10 minutes, reflux for 3 hours, evaporate the solvent and add water to dissolve, extract the organic phase with ether three times, add sodium hydroxide solution to adjust When the pH value was 13-14, the organic phase was washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain 28.2 g of a colorless oil, with a yield of 90%.

[0040]Step B, preparing p-allylphenol, which is divided into...

Embodiment i

[0042] Under nitrogen protection, add 5ml of anhydrous tetrahydrofuran to cover 0.24g (10mmol) of magnesium chips, add dropwise 2 drops of p-bromophenoxymethyl ether obtained in step A, add 1 grain of iodine, and stir for 5-10 minutes. See that the color fades, add 1.8g (8.29mmol) p-bromobenzyloxymethyl ether solution diluted with 10ml tetrahydrofuran dropwise evenly within 10 minutes, add 2ml tetrahydrofuran, and keep stirring at 50°C for 1 hour to obtain the obtained Add the Grignard reagent dropwise into a flask containing 1.5g (12.4mmol) allyl bromide, reflux for 4 hours, stop the reaction, cool to room temperature, add dropwise 40ml of 3mol / L hydrochloric acid solution for 2 hours, stop the reaction Separate the tetrahydrofuran phase, extract the organic phase with ether three times, wash the organic phase with sodium chloride solution until neutral, dry with anhydrous sodium sulfate, filter, and concentrate the filtrate under normal pressure to obtain a black oil, which i...

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Abstract

The present invention provides a method for synthesizing magnolol. The magnolol is prepared from relatively cheap p-bromophenol, chloromethyl methyl ether and allyl bromide by being subjected to hydroxy protection and Grignard reaction to obtain allylphenol intermediate product; dissolving allylphenol into solvent; and carrying out oxidation coupling reaction in the presence of oxidation catalyst and introducing air or oxygen. The method is characterized in that the adopted catalyst is hydroxy*tetramethyl ethylene diamine copper (I) dichloride and has a molecular formula of [Cu(OH) / TMEDA]2Cl2, which allows p-allylphenol to carry out oxidation coupling reaction effectively and solves the problem of difficulty in industrial production of magnolol chemical synthesis; and the total yield of the synthesized magnolol product can reach 50%. The method has the advantages of simple synthetic process, high yield and low cost, and can be applied in industrial production. Comparing test results of infrared detection and high performance liquid phase analysis and detection with those of the magnolol product extracted from plants, the synthesized magnolol product has the similar or the same structure.

Description

technical field [0001] The invention relates to a synthesis method of magnolol, in particular to using an oxidation catalyst to synthesize magnolol through an oxidative coupling reaction of p-allyl phenol. Background technique [0002] Magnolol, also known as magnolol, is one of the important components extracted from magnolia bark. In recent decades, chemists have successively isolated magnolol and honokiol from various plants. Magnolia officinalis is a natural Chinese herbal medicine with a wide range of uses. It has pharmacological effects such as anti-inflammatory, antibacterial, anti-oxidant, anti-tumor, and inhibition of morphine withdrawal. It is known as Sanmu medicinal materials and is one of the important medicinal materials managed by the state plan. [0003] The distribution of Magnolia officinalis in my country is very wide, the market demand is large, and the market price is relatively expensive. At present, magnolol mainly relies on extraction from plants. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/16B01J31/22C07C39/21B01J31/28
CPCY02P20/52
Inventor 郑昌戈罗凤平罗安东
Owner JIANGNAN UNIV
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