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A kind of preparation method of myrtle alkanal

A technology of myrtle alkanal and myrtle alkanol, which is applied in the field of organic synthesis, can solve the problems of complex myrtle alkanal preparation process, high preparation cost, and difficult availability of raw materials, and achieve high yield and low preparation cost. Cost, effect of mild reaction conditions

Active Publication Date: 2017-03-29
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the defects in the prior art such as complex preparation process of myrtle alkanal, high preparation cost and difficult acquisition of raw materials, the invention provides a method for preparing myrtle alkanal

Method used

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  • A kind of preparation method of myrtle alkanal
  • A kind of preparation method of myrtle alkanal
  • A kind of preparation method of myrtle alkanal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of myrtanol:

[0043] Add 55.3g β-pinene (0.4mol, purity 98.5%), 5.92g sodium borohydride (0.15mol, purity 96%), 28.67g trifluoride Boron ethyl ether solution (0.2mol, purity 46.8-47.8%) and 200mL of tetrahydrofuran were reacted at 0-5°C for 6h to obtain dimyrtyl boron, and the next step reaction was continued without separation; After adding 30mL of ethanol to quench the hydroboration reaction, add 68mL of 3mol / L sodium hydroxide aqueous solution and 60mL of 30% hydrogen peroxide solution successively, and react at 40-45°C for 3h. After the reaction was finished, add sufficient saturated aqueous sodium thiosulfate solution to remove excess hydrogen peroxide, separate liquid, wash with water, wash with saturated saline, dry over anhydrous sodium sulfate, and evaporate the solvent to obtain 57.5 g of myrtle alkanol with a purity of 96.8%, yield 90.3%. Structural characterization: IRv: 3313cm -1 (O-H),1041cm -1 (C-O); 1 H NMR (300MHz, CDCl 3 )δ: 1 H NMR (...

Embodiment 2

[0045] Synthesis of myrtanol:

[0046] Add 55.3g β-pinene (0.4mol, purity 98.5%), 7.88g sodium borohydride (0.2mol, purity 96%), 28.67g trifluoride Boron ethyl ether solution (0.2mol, purity 46.8-47.8%) and 200mL of tetrahydrofuran were reacted at 5-10°C for 8h to obtain dimyrtyl boron, and the next step reaction was continued without separation; After adding 30mL of ethanol to quench the hydroboration reaction, add 92mL of 3mol / L sodium hydroxide aqueous solution and 90mL of 30% hydrogen peroxide solution successively, and react at 40-45°C for 3h. After the reaction was finished, add sufficient saturated aqueous sodium thiosulfate solution to remove excess hydrogen peroxide, separate liquid, wash with water, wash with saturated saline, dry over anhydrous sodium sulfate, and evaporate the solvent to obtain 57.9 g of myrtle alkanol with a purity of 96.1%, yield 90.2%. Structural characterization: IRv: 3313cm -1 (O-H),1041cm -1 (C-O); 1 H NMR (300MHz, CDCl 3 )δ: 1 H NMR (...

Embodiment 3

[0048] Synthesis of myrtanol:

[0049] Add 55.3g β-pinene (0.4mol, purity 98.5%), 5.92g sodium borohydride (0.15mol, purity 96%), 28.67g trifluoride Boron ethyl ether solution (0.2mol, purity 46.8-47.8%) and 200mL of tetrahydrofuran were reacted at 0-5°C for 6h to obtain dimyrtyl boron, and the next step reaction was continued without separation; After adding 30 mL of ethanol to quench the hydroboration reaction, add 63.4 g of sodium perborate tetrahydrate (0.4 mol, purity 97%), and react at 30-35° C. for 3 h. After the reaction, add enough saturated aqueous sodium thiosulfate solution to remove excess hydrogen peroxide, separate liquid, wash with water, wash with saturated saline, dry over anhydrous sodium sulfate, and evaporate the solvent to obtain 58.1 g of myrtle alkanol with a purity of 96.7 %, yield 91.1%. Structural characterization: IRv: 3313cm -1 (O-H),1041cm -1 (C-O); 1 H NMR (300MHz, CDCl 3 )δ: 1 H NMR (300MHz, CDCl 3 )δ: 3.55(dd,J=7.6,5.2Hz,2H),2.44-2.31(m...

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Abstract

The invention discloses a preparation method of myrtanal. The method sequentially comprises the following steps: 1, carrying out a hydroboration-oxidation reaction on beta-pinene to generate myrtanol; and 2, carrying out a selective oxidation reaction on myrtanol and active dimethyl sulphoxide to generate myrtanal. Myrtanol is synthesized in a high efficiency manner through hydroboration-oxidation of beta-pinene as a raw material, and the yield is greater than 90%; myrtanal is prepared through selective oxidation of the active dimethyl sulphoxide at room temperature, and the yield is greater than 80%, so the total yield of conversion from the initial raw material beta-pinene to myrtanal is greater than 72%. Compared with present methods, the method disclosed in the invention has the advantages of cheap and easily available reaction raw materials, mild reaction conditions, high purity and high yield of the above obtained product, and great reduction of the preparation cost of myrtanal.

Description

technical field [0001] The invention relates to a preparation method of myrtle alkanal, which belongs to the field of organic synthesis. Background technique [0002] Myrtle alkanal widely exists in plants such as myrtle, lotus magnolia, and Polygonum spicosa, and has potential antibacterial activity, antiviral activity, and blood pressure lowering effect in mammals. In addition, in the field of organic synthesis, myrtle alkanal is an important precursor compound, and a large number of derivative compounds with potential antibacterial, antiviral or antitumor activities can be synthesized through various reaction pathways. [0003] Currently, various methods for the synthesis of myrtle alkanals have been reported. One of the methods is to synthesize the epoxide of β-pinene through a rearrangement reaction to synthesize myrtle alkanal. This synthesis method is to first synthesize the epoxide of β-pinene with β-pinene, and then catalyze it with Lewis acid. Under the rearrange...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/347C07C45/29
CPCC07C29/48C07C45/29C07C2602/42C07C47/347C07C31/137
Inventor 宋湛谦廖圣良商士斌饶小平沈明贵司红燕宋杰
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY