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Synthesis method of tetradec-2-yn-1-ol

A synthesis method, fourteen-carbon technology, applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve the problems of high complexity of operation, harsh reaction conditions, difficult scale-up production, etc., to achieve purity and yield High efficiency, few reaction steps and short time

Active Publication Date: 2019-10-01
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012]This reaction needs to be carried out under strict anhydrous and oxygen-free conditions at minus 78°C. The reaction conditions are harsh, the operation is highly complicated, and there are certain safety hazards, so it is difficult to realize scale-up production; therefore, it is of great practical significance to develop an efficient and safe method for synthesizing 2-tetradecyn-1-alcohol and realize its industrial production

Method used

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  • Synthesis method of tetradec-2-yn-1-ol
  • Synthesis method of tetradec-2-yn-1-ol
  • Synthesis method of tetradec-2-yn-1-ol

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add 40g of powdered sodium hydroxide and 600mL of tetrahydrofuran into the reaction bottle, and slowly introduce dry acetylene gas at about 15°C under stirring, and stop the acetylene gas for about 1 hour; control the temperature below 30°C, and add 50g of 1-bromo Undecane / 100mL tetrahydrofuran solution, after the dropwise addition, continue to stir for 5h.

[0032] Add 30g of dry paraformaldehyde, heat to 60°C and react for 2h; concentrate to remove the solvent, add 250mL of water, extract with dichloromethane for 3 times, combine the organic phases, dry, concentrate, and purify the residue by column chromatography (eluent is petroleum ether : ethyl acetate=10: 1), obtain white solid 36g, purity 99.1%, fusing point: 42-43 ℃; Product 2-tetradecyn-1-alcohol nuclear magnetic detection spectrum result is as follows figure 1 shown. Depend on figure 1 It can be seen that 1 H-NMR (400MHz, CDCl 3 )δ0.88(t, J=8Hz, 3H), 1.20-1.36(m, 16H), 1.48-1.52(m, 2H), 1.60(br, 1H), 2.19...

Embodiment 2

[0034] Add 66g of powdered potassium hydroxide (85%) and 800mL of methyl tert-butyl ether into the reaction flask, slowly introduce dry acetylene gas at about 15°C under stirring, and stop the introduction of acetylene gas after the system is saturated for about 1 hour; Below ℃, add 50g 1-bromoundecane / 200mL methyl tert-butyl ether solution dropwise, and continue stirring for 5h after the dropwise addition.

[0035] Add 50 g of dry paraformaldehyde, heat and reflux for 2 h; cool, add 300 mL of water, stir, separate liquids, dry the organic phase, concentrate, and purify the residue by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1 ) to obtain 28g of white solid with a purity of 98.6% and a melting point of 42-44°C.

Embodiment 3

[0037] Add 1L of 1.6mol / L isopropylmagnesium bromide / tetrahydrofuran solution into the reaction flask, cool to 0°C, slowly introduce 20g of dry acetylene gas, and stir for 1h; control the temperature below 20°C, and add 85g of 1-bromo Undecane / 400mL tetrahydrofuran solution, after the dropwise addition, continue to stir for 5h.

[0038] Control the temperature below 10°C, heat 50g of dry paraformaldehyde to 220°C for decomposition, and pass the formaldehyde gas generated by the decomposition into the above reaction solution; heat to reflux for 30min, cool, concentrate to remove the solvent, add 500mL of 10% hydrochloric acid, and extract with dichloromethane Three times, the organic phases were combined, dried, concentrated, and the residue was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1) to obtain 68 g of a white solid with a purity of 99.5% and a melting point of 43-44°C.

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Abstract

The invention discloses a synthesis method of tetradec-2-yn-1-ol and belongs to the technical field of chemical industry production. According to the method, with acetylene as an initial raw material,the acetylene and alkali react in a solvent to generate acetylene salt; then, 1- bromoundecane is added for a reaction to obtain 1-tridecyne, the thirteen acetylene salt further reacts with paraformaldehyde or a formaldehyde aqueous solution or formaldehyde gas, and through a one-pot method, the tetradec-2-yn-1-ol is synthesized. The synthesis method is mild in reaction condition, easy and convenient to implement and low in production cost, has good economic benefits and can be applied and popularized, and the purity and yield of the product tetradec-2-yn-1-ol are high.

Description

technical field [0001] The invention belongs to the technical field of chemical production, and in particular relates to a synthesis method of 2-tetradecyn-1-ol. Background technique [0002] The American white moth Hyphantria cunea (Drury) belongs to the order Lepidoptera and the family Arctiidae, and is an important international quarantine pest. Because it has the characteristics of miscellaneous feeding habits, large food intake, strong reproductive ability, wide adaptability, fast transmission speed, and serious harm, it has become a major invasive alien pest in my country and the most dangerous invasive species at home and abroad. [0003] The American white moth is native to Beiguan, distributed between 19° and 55° north latitude, and then spread to Europe and Asia. Since the first discovery of the American white moth in Dandong City, Liaoning Province in 1979 in China, its epidemic area has spread to 586 county-level administrative regions in 13 provinces (municipal...

Claims

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Application Information

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IPC IPC(8): C07C29/42C07C33/042
CPCC07C29/42C07C33/042
Inventor 郝德君陈宏健于晓航
Owner NANJING FORESTRY UNIV
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