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Synthesis method of shikimic acid

A synthesis method and technology of shikimic acid are applied in chemical instruments and methods, preparation of carboxylate, preparation of oxygenated compounds, etc., can solve problems such as low optical purity, low total yield, complicated operation, etc., and achieve a simple and easy method. performance, cost reduction, and simple operation

Inactive Publication Date: 2013-11-27
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the synthesis of shikimic acid has been greatly developed, most of them have disadvantages such as long steps, low overall yield, complicated operation or low optical purity. Therefore, it is necessary to further develop a simple and effective shikimic acid synthesis process

Method used

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  • Synthesis method of shikimic acid
  • Synthesis method of shikimic acid
  • Synthesis method of shikimic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add dry triethylamine (33mL, 240mmol) and anhydrous zinc chloride powder (0.9g, 6mmol) into a 250mL three-necked flask, stir the reaction system at room temperature for 1 hour, then add crotonaldehyde (14g, 200mmol) 100mL ether solution, after stirring for 5 minutes, trimethylchlorosilane (29mL, 230mmol) was added dropwise, and the dropwise addition was completed within half an hour. The reaction system was refluxed overnight and cooled to room temperature, then diluted with 100 mL of dry petroleum ether, the organic liquid was filtered through a short (4 cm) alumina column, the filtrate was concentrated, and the colorless liquid was obtained by distillation under reduced pressure (26 g, yield: 92% ), boiling point: 131°C; 1 H-NMR (CDCl 3 ,400MHz):δ6.54(d,J=11.9Hz,1H),6.22(ddd,J=10.3,6.5,4.3Hz,1H),5.73(dd,J=11.9,11.1Hz,1H),4.99( m,1H), 4.83(d,J=10.3Hz,1H),0.22(s,9H). It shows that the colorless liquid is 1,3-butadienyl trimethylsilyl ether shown in structural formula...

Embodiment 2

[0042] Add 1,3-butadienyl trimethylsilyl ether (15 g, 105 mmol) shown in structural formula 1 and 14.5 g (100 mmol) of 3-nitro-acrylic acid ethyl alcohol shown in structural formula 2 in a 250 mL three-necked flask Esters, the reaction system was vigorously stirred at room temperature for 4 hours (track the reaction with gas chromatography), after the reaction was complete, stop stirring and add 50mL methanol to dissolve, then add potassium fluoride (8.7g, 150mmol) and continue stirring for 2 hours, stop stirring and add 50mL tetrahydrofuran and 1,8-Diazabicyclo[5.4.0]undec-7-ene (21.2 g, 140 mmol) was reacted at room temperature for 3 hours and the reaction was stopped. The reaction system was quenched by adding 50 mL of water, extracted three times with ethyl acetate (50 mL), and the combined organic phases were first washed with 10% aqueous hydrochloric acid (20 mL) with a concentration of 10% by mass, and then washed with saturated aqueous sodium bicarbonate and saturated b...

Embodiment 3

[0044] Except that 85mL of ethanol was used instead of 50mL of methanol in Example 2 and potassium fluoride was added to react at 50°C for 10 hours, the rest of the operating steps were the same as in Example 2 to obtain 3-hydroxyl-1,4-cyclohexane di Ethyl-1-carboxylate, yield 61%, product characterization data with embodiment 2.

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Abstract

The invention discloses a synthesis method of shikimic acid, which is started from the common low-cost chemical material crotonaldehyde, is prepared by four steps of simple reaction operations including Diels-Alder reaction, Sharpless asymmetric epoxidation reaction and the like, has the total yield of 22%, can be used for synthesizing the shikimic acid with the purity reaching up to more than 98% ee, and ensures the product purity to meet the conventional demand. The reagent used by the synthesis method is economical and safe; the synthesis method is short in steps and simple and easy in operation, and particularly uses the 'one-pot reaction' step twice, thus reducing 'the three wastes' emission and the environmental pollution; and therefore, the synthesis method of the shikimic acid is in accordance with the social development tendency of energy conservation and emission reduction, and is efficient and environment-friendly.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for synthesizing shikimic acid. Background technique [0002] The molecular formula of shikimic acid is C 7 h 10 o 5 , the chemical name is [3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid, the structural formula is as follows: [0003] [0004] Shikimic acid [(-)-Shikimic acid] is an organic compound isolated from Japanese "Shikimic acid" in 1885. Later, it was found that it also exists in plants such as star anise, tomato leaves, and hypericum. Among them, it is used in traditional Chinese medicine "Star anise" has the highest content. Early shikimic acid was mostly prepared by extracting star anise as raw material. For example, Chinese patent ZL200710021150.0 discloses a convenient and effective shikimic acid production method, which is a method of directly extracting shikimic acid from plant raw material star anise. Method; Chinese patent app...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C62/32C07C51/367C07C27/02
Inventor 朱钢国崔伟剑夏思苑何祖莺
Owner ZHEJIANG NORMAL UNIVERSITY
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