Unlock instant, AI-driven research and patent intelligence for your innovation.

Synthesis process of 3, 4-methylenedioxyphenol

A technology of dioxyphenol and synthesis process, applied in 3 fields, can solve the problems of low yield and difficult separation, and achieve the effects of reducing the difficulty of rectification, simplifying the process flow, and mild reaction conditions

Pending Publication Date: 2021-10-29
绵阳三香汇生物科技有限公司
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In view of the above-mentioned shortcoming of the prior art, the purpose of the present invention is to provide a kind of synthesis technique of 3,4-methylenedioxyphenol, for solving the problem of 3,4-methylenedioxyphenylbenzene in the prior art The preparation of sesamol from ketone has the problems of low yield and difficult separation

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis process of 3, 4-methylenedioxyphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A kind of synthetic technique of 3,4-methylenedioxyphenol, comprises the steps:

[0029] S1. Add 30g (0.225mol) of anhydrous aluminum chloride, 200g (1.961mol) of acetic anhydride and 450g (3.685mol) of piperonine into a three-necked flask, start stirring, raise the temperature to 60°C, and react for 4 hours. After the reaction is completed, use 200g Washing twice with water, and the washed material was distilled under reduced pressure to recover piperonylcycline to obtain the acylation intermediate 3,4-methylenedioxyacetophenone with a mass yield of 121%;

[0030]S2. Add 3,4-methylenedioxyacetophenone into a 1000ml three-necked flask, then sequentially add 15g dilute sulfuric acid (49wt%), 150g (2.498mol) acetic acid, and 200g dichloroethane, and heat up to 40°C in a water bath , dropwise add 380g (3.017mol) hydrogen peroxide (27wt%), continue to react at this temperature for 6h after dropping, after the reaction, the organic phase is recovered by rotary evaporation to...

Embodiment 2

[0034] A kind of synthetic technique of 3,4-methylenedioxyphenol, comprises the steps:

[0035] S1. Add 40g (0.301mol) of anhydrous zinc chloride, 200g (1.961mol) of acetic anhydride and 450g (3.685mol) of piperonine into a three-necked flask, start stirring, raise the temperature to 80°C, and react for 5 hours. After the reaction is completed, use 200g Washing twice with water, after the washing, the material is distilled under reduced pressure to recover the piperonyl ring to obtain the acylation intermediate 3,4-methylenedioxyacetophenone;

[0036] S2. Add 3,4-methylenedioxyacetophenone into a 1000ml three-necked flask, then sequentially add 20g dilute sulfuric acid (49wt%), 200g (3.331mol) acetic acid, and 200g dichloromethane, and heat up the water bath to 45°C. Add 400g (3.176mol) of hydrogen peroxide (27wt%) dropwise, and continue to react at this temperature for 5h after the drop is completed. After the reaction, the organic phase is recovered by rotary evaporation to ...

Embodiment 3

[0039] A kind of synthetic technique of 3,4-methylenedioxyphenol, comprises the steps:

[0040] S1. Add 40g (0.301mol) of anhydrous zinc chloride, 300g (2.941mol) of acetic anhydride and 450g (3.685mol) of piperonine into a three-necked flask, start stirring, raise the temperature to 70°C, and react for 5 hours. After the reaction is completed, use 200g Washing twice with water, after the washing, the material is distilled under reduced pressure to recover the piperonyl ring to obtain the acylation intermediate 3,4-methylenedioxyacetophenone;

[0041] S2. Add 3,4-methylenedioxyacetophenone into a 1000ml three-necked flask, then sequentially add 20g dilute sulfuric acid (49wt%), 260g (4.3303mol) acetic acid, and 200g dichloromethane, and heat up to 50°C in a water bath. Add 580g (4.605mol) hydrogen peroxide (27wt%) dropwise, and continue to react at this temperature for 5h after the drop is completed. After the reaction, the organic phase is recovered by rotary evaporation to r...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention relates to the technical field of compound synthesis, particularly to a synthesis process of 3, 4-methylenedioxyphenol. The synthesis process comprises the following steps of: adding 3, 4-methylenedioxyacetophenone, a second catalyst and a first solvent into a reaction kettle, adding an oxidizing agent, carrying out a reaction for 4-8 h at a temperature of 25-50 DEG C, and carrying out phase separation recovery on the first solvent; and adding prepared 3, 4-methylenedioxyphenol acetate, the second solvent and a sodium hydroxide solution into the reaction kettle, reacting at 20-60 DEG C for 2-6 hours, and adjusting the pH value to 3-6 to obtain the 3, 4-methylenedioxyphenol. With the synthesis process adopted, the problems of low yield and high separation difficulty in preparation of sesamol from 3, 4-methylenedioxyacetophenonein the prior art are solved. According to the synthesis process, benzodioxole is taken as a starting raw material, synthesis is carried out in three steps, the raw material conversion rate is high, no other side reaction exists, the reaction conditions are mild, safety and environmental protection are achieved, the production cost is low, and the product quality is excellent.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a synthesis process of 3,4-methylenedioxyphenol. Background technique [0002] 3,4-methylenedioxyphenol, also known as sesamol, is an important aroma component of sesame oil and an important quality stabilizer of sesame oil. Sesamol has excellent antioxidant capacity and is often used as an antioxidant in food and medicine. At the same time, it is an important raw material for the synthesis of antihypertensive drugs and cardiovascular drugs, and it is also a raw material for the pesticide piperonyl butyl ether. Sesamol is currently in great demand in the field of drug synthesis. [0003] There are three main synthetic techniques for sesamol: one is extraction from sesame oil, the other is total synthesis with piperonamine, and the third is semi-synthetic route from 3,4-methylenedioxyacetophenone. Extracting sesamol from sesame oil consumes a lot of solvents, and the ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D317/64
CPCC07D317/64
Inventor 王凯马妙玲熊智李良龙
Owner 绵阳三香汇生物科技有限公司