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8, 9-dihydrocannabidiol as well as synthesis method and application thereof

A technology for cannabidiol and synthesis method, which is applied in chemical instruments and methods, active ingredients of hydroxyl compounds, organic compounds/hydrides/coordination complex catalysts, etc., and can solve the problem of large amount of catalysts and the like

Active Publication Date: 2021-09-10
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved in the present invention is to provide a new synthetic method of 8,9-dihydrocannabidiol to solve the problem that catalyst consumption is more in the existing 8,9-dihydrocannabidiol synthetic method

Method used

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  • 8, 9-dihydrocannabidiol as well as synthesis method and application thereof
  • 8, 9-dihydrocannabidiol as well as synthesis method and application thereof
  • 8, 9-dihydrocannabidiol as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Olivetol (18g, 0.1mol) and α-phellandrene (17g, 0.125mol) were dissolved in toluene (10mL), ferric chloride (0.162g, 1mmol) was added, and the mixture was heated at room temperature (25°C) The reaction was stirred, monitored by TLC and HPLC, until the yield of 8,9-dihydrocannabidiol no longer increased, filtered, and the resulting filtrate was washed with saturated brine (3×50mL), and the solvent was distilled off under reduced pressure, the crude product Separation by silica gel column chromatography, and elution with a mixture of petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 40:1), followed by TLC elution detection. The eluate from the silica gel column containing the target product was collected and concentrated to obtain 8,9-dihydrocannabidiol (28.44 g, yield 90%) as a dark yellow oil. The specific proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the obtained H2CBD are shown in figure 1 with figure...

Embodiment 2-8

[0043] Embodiment 2-8, comparative example 1-2: the impact of catalyst on yield

[0044] The synthesis methods of Examples 2-8 and Comparative Examples 1-2 are similar to those of Example 1, except that the catalysts used are different. The Lewis acid catalysts used in each embodiment and comparative examples and the corresponding yields are shown in Table 1.

[0045] The catalyst that table 1 embodiment 1-10 adopts and corresponding yield

[0046] catalyst Yield (%) Example 1 Ferric chloride 90 Example 2 Boron trifluoride monohydrate 53 Example 3 Boron trifluoride diethyl ether 53 Example 4 Ferric chloride hexahydrate 50 Example 5 Aluminum trichloride 54 Example 6 Copper Chloride Dihydrate 38 Example 7 ferric bromide 41 Example 8 tin chloride 33 Comparative example 1 nickel chloride Trace (<5)

[0047] As can be seen from the results in Table 1, the synthetic method of the present invention n...

Embodiment 9

[0048] Embodiment 9: the influence of the consumption of catalyst iron trichloride on yield

[0049] The synthetic method of Example 9 and the synthetic method of Comparative Example 3 are similar to that of Example 1, except that the amount of catalyst is different. The amount of catalyst used in each embodiment and the corresponding yield are shown in Table 2.

[0050] Table 2 embodiment 1, the catalyst consumption that 9 and comparative example 3 adopt and corresponding yield

[0051] Ferric chloride dosage (wt%) Yield (%) Example 9 0.45 65 Example 1 0.9 90 Comparative example 3 4.5 89

[0052] As can be seen from the results in Table 2, along with the increase of ferric chloride consumption, the yield also increases thereupon; when the consumption of ferric chloride was 0.9%, the yield reached the highest 90%; The consumption of iron, the product yield can not continue to increase; And the consumption of ferric trichloride exceeds 4...

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Abstract

The invention discloses 8, 9-dihydrocannabidiol as well as a synthesis method and an application thereof, and belongs to the field of organic synthesis. According to the invention, alpha-phellandrene and olive alcohol are taken as substrates, and under the action of a Lewis acid catalyst, 8, 9-dihydrocannabidiol is obtained through reaction. The raw materials are cheap, the used catalyst is cheap and easy to separate (filter removal), the usage amount is small (0.9% of the mass of reactants), the catalyst is mild (Lewis acid), the yield is high (90%), the industrialization cost is greatly reduced, and the operation is simple.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to 8,9-dihydrocannabidiol and its synthesis method and application. Background technique [0002] Natural compounds extracted from the cannabis plant possess various biological activities, including bacteriostatic properties. Cannabis plants contain more than 500 chemical substances, including about 100 cannabinoids and various other terpenes, phenols, lipids, flavonoids and steroids, among which tetrahydrocannabinol (THC, which has hallucinogenic effects on the human body, And make the human body have adverse symptoms such as rapid heartbeat, drowsiness, dry mouth and excessive appetite) and cannabidiol (CBD, which has been approved for use in food and cosmetics in the United States) are the two most important cannabinoids present in the cannabis plant. However, because CBD can be converted into the drug THC by chemical means, CBD is still not allowed to be us...

Claims

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Application Information

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IPC IPC(8): C07C37/14C07C39/23B01J27/135B01J27/10B01J27/122B01J27/125B01J27/128B01J31/22A61K31/05A61P31/04
CPCC07C37/14C07C39/23B01J27/135B01J27/10B01J27/122B01J27/125B01J27/128B01J31/2208A61K31/05A61P31/04C07C2601/16
Inventor 夏咏梅吴淇邹亮华郭茂岳胡学一方云
Owner JIANGNAN UNIV
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