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A kind of preparation method of 3,4-methylenedioxyphenol

A technology of dioxyphenol and dioxyacetophenone, which is applied in the field of preparation of heterocyclic compounds, can solve the problems of low yield and high cost of raw materials, and achieves the effects of high yield, simple operation and broad application prospect.

Active Publication Date: 2022-03-15
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material cost that this method adopts is high, and yield is on the low side

Method used

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  • A kind of preparation method of 3,4-methylenedioxyphenol
  • A kind of preparation method of 3,4-methylenedioxyphenol
  • A kind of preparation method of 3,4-methylenedioxyphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Put 100ml of toluene, 36g of formic acid, and 36g of 3,4-methylenedioxyacetophenone into a four-necked reaction flask, stir and heat to 30-40°C, and keep for 30 minutes; slowly add 36g of 50% hydrogen peroxide dropwise, and the dropping time 12 hours.

[0038] After the dropwise addition, keep stirring for 1 hour, then let stand for 30 minutes, remove the lower layer of acid water, wash the toluene layer with 50ml of water, remove the lower layer of water, desolvate the toluene layer under reduced pressure, remove all the toluene, and use the residue for future use.

[0039] Add 140ml of water and 60g of 30% liquid caustic soda into the four-necked reaction flask, add the raffinate obtained in the previous step, and stir and react at 35-40°C for 4 hours. After the reaction is completed, add 10% hydrochloric acid to adjust the pH value to 6-6.5 , and stirred for 1 hour.

[0040] Stand still for 30 minutes, remove the lower water layer, collect the oil layer, rectify the...

Embodiment 2

[0045] Put 100ml of toluene, 72g of formic acid, and 36g of 3,4-methylenedioxyacetophenone into a four-necked reaction flask, stir and heat to 30-40°C, and keep it for 30 minutes; slowly add 36g of 50% hydrogen peroxide dropwise, and the dropping time 12 hours. After the dropwise addition, keep stirring for 1 hour, let stand for 30 minutes, remove the lower layer of acid water, wash the toluene layer with 50ml of water, remove the lower layer of water, desolvate the toluene layer under reduced pressure, remove all the toluene, and use the residue for later use.

[0046] Add 140ml of water and 60g of 30% liquid caustic soda into the four-necked reaction flask, add the raffinate in Example 1, stir and react at 35-40°C for 4 hours, when the reaction is over, add 10% hydrochloric acid to adjust the pH to 6~6.5, and stir React for 1 hour. After standing still for 30 minutes, the lower water layer was removed, and the oil layer was collected. The oil layer was rectified under high ...

Embodiment 3

[0048] Put 200ml of toluene, 144g of formic acid, and 72g of 3,4-methylenedioxyacetophenone into a four-necked reaction flask, stir and heat to 30-40°C, and keep for 30 minutes; slowly add 72g of 50% hydrogen peroxide dropwise, and the dropping time 12 hours. After the dropwise addition, keep stirring for 1 hour, let stand for 30 minutes, remove the lower layer of acid water, wash the toluene layer with 100ml of water, remove the lower layer of water, desolvate the toluene layer under reduced pressure, remove all the toluene, and use the residue for future use.

[0049] Add 280ml of water and 120g of 30% liquid caustic soda into the four-necked reaction flask, add the raffinate in Example 3, stir and react at 35-40°C for 4 hours, after the reaction is completed, add 10% hydrochloric acid to adjust the pH to 6~6.5, and stir React for 1 hour. After standing still for 30 minutes, the lower water layer was removed, and the oil layer was collected. The oil layer was rectified unde...

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Abstract

The invention discloses a preparation method of 3,4-methylenedioxyphenol, which is characterized in that 3,4-methylenedioxyacetophenone is used as a starting material, and is added dropwise in toluene and formic acid solution Hydrogen peroxide undergoes an oxidation reaction, and the resulting substance is hydrolyzed, neutralized, and rectified to obtain the target product of 3,4-methylenedioxyphenol. The invention has the advantages of easy-to-obtain raw materials, mild and safe reaction conditions, simple and convenient operation, good product purity and high yield.

Description

technical field [0001] The invention relates to the preparation of a heterocyclic compound, in particular to a preparation method of a heterocyclic compound containing an oxygen atom, especially 3,4-methylenedioxyphenol. Background technique [0002] 3,4-Methylenedioxyphenol, also known as sesamol, is a white crystalline powder with a melting point of 63~65°C. It is an important drug intermediate that can be used to synthesize the antidepressant drug paroxetine. [0003] In the prior art, the synthetic method of 3,4-methylenedioxyphenol mainly contains following two kinds: [0004] One is obtained from piperonamine as raw material through diazotization reaction, hydrolysis and rectification, and its yield is usually 35%. The reaction is as follows: [0005] [0006] For example, in the Chinese invention patent application CN1763032A, a synthetic method of sesamol, a natural food antioxidant, is disclosed. It is disclosed that piperonamine is used as a synthetic precurs...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/64
CPCC07D317/64
Inventor 沈建伟
Owner SUZHOU JINGYE MEDICINE & CHEM
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