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Method for synthesizing 3-tetrahydrofurfuryl alcohol

A tetrahydrofuran methanol, cyclization technology, applied in the synthesis of 3-tetrahydrofuran methanol, the new synthesis field of third-generation nicotinic insecticide intermediates, can solve the problems of increasing product costs, achieve low cost, reduce production costs, The effect of mild reaction conditions

Inactive Publication Date: 2016-01-20
SHIJIAZHUANG XINGBAI BIOLOGICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the synthetic route, metal borohydride is used as reducing agent, which greatly increases product cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1, synthetic 3-tetrahydrofuran methanol

[0025] (1) Add 54g (0.3375mol) of diethyl malonate (0.3375mol) and 227g of 20% potassium tert-butoxide solution in tert-butanol prepared by 54g diethyl malonate and 45.4g potassium tert-butoxide into a 500ml four-necked reaction flask, stir at room temperature for 30 minutes, and control Start to add 46.5g (0.3720mol) of 2-bromoethanol dropwise at a temperature of 25°C to 28°C, raise the temperature to 50°C after dropping, keep the temperature for 1.5 hours, evaporate the solvent with a rotary evaporator below 75°C, and filter with suction to obtain a colorless oily liquid 2 -Hydroxyethyl-diethyl malonate 64.6g (0.3167mol), purity 97% (GC), yield 91%;

[0026] (2) Add 64.6g (0.3167mol) of 2-hydroxyethyl-diethyl malonate into a 500ml four-necked reaction flask, add 76g of 20% sodium hydroxide solution, heat up to 45°C, stir for 2 hours, and cool down To 25°C, add about 69.3g of 20% hydrochloric acid, adjust the pH to ...

Embodiment 2

[0031] (1) Add 54g of diethyl malonate (0.3375mol) and 194.4g of 20% sodium tert-butoxide methanol solution prepared by 38.9g of sodium tert-butoxide into a 500ml four-necked reaction flask, stir at room temperature for 40 minutes, and start 46.5g of 2-bromoethanol was added dropwise, and the temperature was raised to 50°C after dropping, and the reaction was carried out for 2 hours. The solvent was evaporated by a rotary evaporator below 75°C, and 63.2g (0.3304mol ), purity 97% (GC), yield 89%;

[0032] (2) Add 63.2g (0.3304mol) of 2-hydroxyethyl-diethyl malonate into a 500ml four-necked reaction flask, add 72.4g of 20% hydrochloric acid, heat up to 45°C, stir for 3 hours, and cool down to 25°C ℃, add about 79g of 20% sodium hydroxide solution, adjust PH=6-7, evaporate to dryness under reduced pressure below 80℃, filter to obtain 47.1g (0.3106mol) of 2-hydroxyethyl-malonic acid, purity: 95% (GC), yield: 94%;

[0033] (3) Put 47.1g (0.3106mol) of 2-hydroxyethyl-malonic acid,...

Embodiment 3

[0036] (1) Add 54g (0.3375mol) of diethyl malonate (0.3375mol) and 72.9g of a 30% sodium methoxide methanol solution prepared by 21.9g of sodium methoxide into a 500ml four-necked reaction flask, stir at room temperature for 30 minutes, and start adding 2-bromoethanol dropwise 46.2g, the temperature was raised to 50°C after dropping, and the temperature was kept for 1 hour, and the solvent was evaporated by a rotary evaporator below 75°C, and 60.3g (0.2869mol) of 2-hydroxyethyl-diethyl malonate was obtained by suction filtration, with a purity of 97% (GC), yield 85%;

[0037](2) Add 60.3g (0.2869mol) of 2-hydroxyethyl-diethyl malonate into a 500ml four-necked reaction flask, add 69g of 20% sodium hydroxide solution, heat up to 45°C, stir for 3 hours, then cool down To 25°C, add about 63g of 20% hydrochloric acid, adjust PH=6-7, evaporate to dryness under reduced pressure below 80°C, filter to obtain 42.5g (0.2726mol) of 2-hydroxyethyl-malonic acid, purity: 95% ( GC), yield: 9...

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Abstract

The invention relates to a method for synthesizing 3-tetrahydrofurfuryl alcohol. According to the technical scheme, 2-bromoethanol and diethyl malonate serve as starting materials, under the alkaline condition, 2-hydroxyethyl-diethyl malonate is generated through a reaction, hydrolysis is conducted on the 2-hydroxyethyl-diethyl malonate to generate 2-hydroxyethyl-malonate, catalyzing and high-pressure hydrotreatment are conducted on the 2-hydroxyethyl-malonate to generate 2-hydroxymethyl-1,4-butanediol, and dehydration cyclization is conducted on the 2-hydroxyethyl-1,4-butanediol to generate the 3-tetrahydrofurfuryl alcohol. According to the method for synthesizing the 3-tetrahydrofurfuryl alcohol, the yield can reach over 85 percent, the purity can reach above 95 percent, the reaction condition is mild, the cost is low, operation is easy, and the method has the advantage of being suitable for industrial production.

Description

technical field [0001] The invention relates to a new synthesis method of a third-generation neonicotinoid insecticide intermediate, in particular to a method for synthesizing 3-tetrahydrofuran methanol, which belongs to the technical field of veterinary medicine. Background technique [0002] 3-tetrahydrofuran methanol is an important intermediate for the synthesis of the third-generation nicotinic insecticide dinotefuran. Dinotefuran was developed by Mitsui Corporation of Japan. It was first registered and listed in Japan in 2002, and has been approved in many countries. Pesticide registration, dinotefuran has the characteristics of high efficiency, broad spectrum, good systemic permeability, and is safe to aquatic organisms, birds, and mammals. It is suitable for controlling pests of vegetables, fruit trees, rice and flowers such as Hymenoptera, Diptera, Orthoptera, Beetles, Lepidoptera and Hemiptera. [0003] For the synthesis of 3-tetrahydrofuranmethanol, it is repor...

Claims

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Application Information

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IPC IPC(8): C07D307/12
CPCC07D307/12
Inventor 刘中须暴连群杨伟苏少鹏闫琦
Owner SHIJIAZHUANG XINGBAI BIOLOGICAL ENG