Method for preparing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-formic acid

A technology of hydroxybenzene and tetrahydrofuran, applied in the field of organic compound preparation, can solve problems such as lack of mature technology, and achieve the effects of improving economic benefits, cheap and easy-to-obtain raw materials, and reaction cost advantages

Active Publication Date: 2019-11-15
汉瑞药业(荆门)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there is no mature related technology in China for the synthesis report of 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid

Method used

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  • Method for preparing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-formic acid
  • Method for preparing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-formic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation method of 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid The synthetic route is as follows:

[0033]

[0034] Proceed as follows:

[0035] first step reaction

[0036] Add 4.4g of magnesium powder, elemental iodine and magnetons into a 500mL three-necked flask, add a reflux tube to the middle mouth of the three-necked flask, and use a tee to connect the nitrogen balloon on the reflux tube; install a constant pressure dropping funnel on the left side of the three-necked flask , the constant pressure dropping funnel was equipped with 9.075g of 2,5-dibromotoluene in tetrahydrofuran solution; the right side of the three-necked flask was sealed with a reverse rubber stopper, and the nitrogen was replaced three times; Tetrahydrofuran solvent 150mL, the reaction solution was heated to 50°C, and the tetrahydrofuran solution containing 2,5-dibromotoluene was slowly added dropwise to the reaction solution, and after the dropwise addition, the reaction...

Embodiment 2

[0040] first step reaction

[0041] Add 5.3g of magnesium chips, iodine element and magnetons into a 500mL three-necked flask. A reflux tube is added to the mouth of the three-necked flask, and a drying tube is connected to the reflux tube. A constant-pressure dropping funnel is installed on the left side of the three-necked flask. The dropping funnel is filled with 5.847g of 2,5-dichlorotoluene in tetrahydrofuran solution; add 150mL of freshly treated tetrahydrofuran solvent from the right bottle mouth, heat the reaction solution to 65°C, and dissolve the solution containing 2,5-dichlorotoluene The tetrahydrofuran solution was slowly added dropwise to the reaction solution, and after the dropwise addition, continued to react at 65°C for 8 hours; slowly bubbled carbon dioxide gas into the reaction solution, and at the same time opened the tee to connect to the atmosphere, and stopped blowing after 1 hour of reaction; wait for the reaction solution to cool to room temperature, ...

Embodiment 3

[0044] The difference between the first step reaction and the first step reaction in Example 1 is that 12.4881 g of 2,5-diiodotoluene is used instead of 2,5-dibromotoluene; the reaction is carried out under the protection of argon, and the reaction is carried out at 65°C After 2 hours, 4.2 g of yellow solid was obtained, and the calculated yield was 60%.

[0045] The difference between the second step reaction and the second step reaction of Example 1 is that the chromium trioxide is 8.0g, the reaction time is extended to 12h at 25°C, the extraction solvent is dichloromethane, and the desiccant is anhydrous Magnesium sulfate, 1.5 g of the target compound was obtained, and the calculated yield was 39%.

[0046] The proton NMR spectrum of the product is as follows:

[0047] 1 HNMR (400MHz, DMSO-d 6 )δ13.61(br,1H),8.50-8.0(br,1H),8.20(d,J=8.0Hz,1H),8.17(s,1H),7.95(d,J=8.0Hz,1H), 6.77(s,1H), the spectrum is as figure 1 shown.

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Abstract

The invention discloses a method for preparing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-formic acid. The method disclosed by the invention comprises the following steps: dissolving 2,5-toluene dihalideinto a tetrahydrofuran solution, carrying out a reaction with magnesium metal under iodine catalysis so as to obtain a corresponding Grignard reagent, and introducing carbon dioxide so as to obtain 2-methylterephthalic acid; performing chromium trioxide oxidation and diluted hydrochloric acid hydrolysis on the 2-methylterephthalic acid in the presence of glacial acetic acid, acetic anhydride andconcentrated sulfuric acid so as to prepare the 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-formic acid. The preparation method disclosed by the invention is simple in synthesis, cheap and readily available in raw material and convenient for large-scale preparation, reaction treatment in the invention is simple, and a pure target product can be obtained by virtue of washing, extracting and filtering only. Moreover, requirements on reaction instruments and equipment are simple, and since the raw materials are cheap and readily available, the method has great advantages on reaction cost, improves economic benefits and has excellent industrial prospects.

Description

technical field [0001] The invention relates to the technical field of organic compound preparation, in particular to a preparation method of 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid. Background technique [0002] Terephthalic acid compounds are an important class of dyes, drugs and chemical intermediates. It has potential application value in the field of synthesis of multifunctional metal-organic frameworks (MOFs). Pre-modification of organic active functional groups on the side of terephthalic acid is a common research strategy. The introduction of new functional groups, especially chemically active groups, brings new properties to this type of new materials. [0003] BaogangWang et al reported the synthesis of 2-formyl terephthalic acid from 2-formyl benzoic acid with different substituents in 2014, but the yield of 2-formyl terephthalic acid synthesis was very low at 20%, from the author According to the NMR data provided, the obtained material is also ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/89
CPCC07D307/89
Inventor 席福贵董智云赵三虎范建凤董芝彤张佳琪
Owner 汉瑞药业(荆门)有限公司
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