Magnolol synthesizing method

A synthesis method and a technique for honokiol, applied in the field of honokiol synthesis, can solve the problems of harsh synthesis conditions, low yield of honokiol, no industrial practicability, etc., and achieve high yield, low cost, and synthesis process. simple effect

Inactive Publication Date: 2008-10-29
JIANGNAN UNIV
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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 is to prepare p-bromobenzyl methyl ether: p-bromophenol is dissolved in an acetone solvent, potassium carbonate and chloromethyl methyl ether (MOMCl) are added, and p-bromobenzyl methyl 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-bromobenzyl methyl ether prepared in the first step is reacted with allyl bromide under the participation of tetrahydrofuran solvent and magnesium chips to obtain p-allyl phenol Propylphenol; the expression of its reaction is as follows:

[0027]

[0...

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-bromobenzyl methyl ether: put 25g (0.1445mol) p-bromophenol in a flask, add 200 ml of acetone, dissolve p-bromophenol in acetone, then add 17.5g (0.127mol) potassium carbonate After stirring for 15 minutes, 15 g (0.185 mol) of chloromethyl methyl ether was evenly added dropwise within about 10 minutes, and refluxed for 3 hours. After the solvent was evaporated, water was added to dissolve it, and the organic phase was extracted three times with ether, and the pH was adjusted by adding sodium hydroxide solution. value to 13-14, wash the organic phase with water until neutral, dry with anhydrous sodium sulfate, filter, and concentrate the filtrate to obtain 28.2 g of a colorless oil, with a yield of 90%.

[0040] Step B, preparing p-a...

Embodiment i

[0042] Under the protection of nitrogen, add 5ml of anhydrous tetrahydrofuran to cover 0.24g (10mmol) of magnesium chips, add dropwise 2 drops of p-bromobenzyl methyl 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-bromobenzyl methyl ether solution diluted with 10ml tetrahydrofuran dropwise evenly within 10 minutes, add 2ml tetrahydrofuran, keep stirring at 50°C for 1 hour, the prepared format Add the 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 acid hydrolysis for 2 hours, stop the reaction and separate The tetrahydrofuran phase, the organic phase was extracted 3 times with ether, and then the organic phase was washed with sodium chloride solution to neutrality, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under normal...

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Abstract

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