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Preparation method for dihydrosafrole

A technology of dihydrosafrole and piperonylcycline, applied in the direction of organic chemistry, can solve the problems of easy occurrence of side reactions, low yield, high catalyst activity, etc., and achieve the effect of mild reaction conditions, high total yield, and simple operation process

Inactive Publication Date: 2011-05-25
ZHEJIANG UNIV
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Benefits of technology

This patented technology allows for accurate determination of certain chemicals based on their molecular structure or properties through XRF analysis. It also includes confirmation that these compounds were correctly made from an organic solvent containing piperonium acids called α - hydroxyethyketones. Overall, it provides technical means for accurately identifying specific types of chemicals with unique structures and uses minimal equipment while still producing effective results at reasonable cost levels.

Problems solved by technology

This patents describes different ways to make certain types of compounds called dihosfolds that can act like insect repellants without harmful effects such as being poisonous when consumed at levels above 10 ppm. These techniques involve reacting specific molecules together into one final form beforehand, which makes it easier to manufacturers who want them due to their safety concerns associated with these substance's use.

Method used

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  • Preparation method for dihydrosafrole
  • Preparation method for dihydrosafrole

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Embodiment 1

[0030] Embodiment 1, a kind of synthetic method of dihydrosafrole, take piperonylcycline and propionyl chloride as starting raw material, carry out the following steps successively:

[0031] 1), Friedel-Crafts acylation reaction of piperonyl ring:

[0032] Add 40.0g (0.294mol) of zinc chloride to 100mL (126g) of dichloroethane, control the temperature at 0~5°C, add 24.0g (0.197mol) of piperonyl dropwise, and continue at this temperature after the dropwise addition Add propionyl chloride 22.0g (0.237mol) dropwise. After the dropwise addition, continue to stir at this temperature. During the reaction, take a sample in water and take the lower organic phase for GC tracking detection until the piperonyl ring reaction is complete, about 18 hours. After stopping the reaction. Slowly add the reaction mixture into 200ml of ice water, stir and dissolve, then let it stand for stratification, wash the lower organic phase with water until it is neutral, distill off the solvent dichloroet...

Embodiment 2

[0041] Embodiment 2, a kind of synthetic method of dihydrosafrole:

[0042] Step 1) Solvent I selects tetrachloroethane (replacing ethylene dichloride in Example 1) for use, and the consumption is 100mL (160g), and the catalyst selects ferric chloride (replacing zinc chloride in Example 1), and the reaction The time was 14 hours, the amount of catalyst used (the molar ratio to the raw material was the same as in Example 1) and other operations were the same as in Example 1, and the yield of piperonyl ethyl ketone was 89.3%, and the purity was 96.8%.

[0043] Step 2) is equivalent to Example 1.

[0044] The total yield of the two-step reaction is 81.2%, and the product purity is 94.1%.

Embodiment 3

[0045] Embodiment 3, a kind of synthetic method of dihydrosafrole:

[0046] The amount of catalyst zinc chloride in step 1) is 50g (0.368mol), the amount of propionyl chloride is 25g (0.270mol), and the reaction time is 12 hours. Other operations are the same as in Example 1, and the yield of piperonyl ethyl ketone is 92.3%. , with a purity of 98.8%.

[0047] Step 2) is equivalent to Example 1.

[0048] The total yield of the two-step reaction is 84.1%, and the product purity is 98.9%.

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Abstract

The invention discloses a preparation method for dihydrosafrole. Piperidine and propionyl chloride are used as initial raw materials, and the preparation method comprises the following steps of: 1) acylation reaction of Friedel-crafts of the piperidine: reacting the piperidine and the propionyl chloride in a solvent I under the catalytic action of a lewis acid catalyst, adding iced water after finishing the reaction, standing, separating phases, washing an organic phase in the lower layer and distilling the solvent I to obtain piperonyl ethyl ketone; and 2) reduction reaction of Wolff-Kishner-Huang-min-lon of the piperonyl ethyl ketone: refluxing the piperonyl ethyl ketone and hydrazine hydrate solution at the mass concentration of 80 to 90 percent in a solvent II for hydrazone reaction, and adding polyethyleneglycol-400 and potassium hydroxide and performing hydrazone decomposing reaction to obtain the dihydrosafrole. The method for preparing the dihydrosafrole has the characteristics of high product yield rate, mild process condition, simple operation and the like.

Description

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Claims

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Application Information

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Owner ZHEJIANG UNIV
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