Method for synthesizing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid

A technology of hydroxybenzene and dihydrogen, applied in the field of organic synthesis, can solve the problems of undeveloped methods and related patents, and achieve the effects of short reaction time, easy availability of raw materials, and simple post-processing

Active Publication Date: 2019-12-03
XINZHOU TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] At present, there are no mature methods and related patents for the synthesis of 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid.

Method used

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  • Method for synthesizing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid
  • Method for synthesizing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid
  • Method for synthesizing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation method of 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid, the steps are as follows:

[0043](1) Add 2,5-dibromotoluene (14.5g, 0.058mol), glacial acetic acid (87.07g, 1.45mol), acetic anhydride (77.8g, 0.76mol), concentrated sulfuric acid (30.8g, 0.31mol) in sequence In a 250mL single-necked flask, the reaction system was cooled to 0-5°C in an ice-water bath. Under vigorous stirring, chromium trioxide (17.5g, 0.175mol) was slowly added in batches, and the addition process lasted for 30min. The reaction temperature was controlled by an ice-water bath at 0-5°C; the final reaction solution continued to stir at this temperature for 2h, and then Under stirring for 2h. The reaction solution was slowly poured into ice water (850mL), and stirred rapidly, a large amount of light green solid appeared, placed in ultrasonic vibration for 20min, and suction filtered to obtain a light green solid, which was washed in batches with 200mL deionized water, and t...

Embodiment 2

[0049] The preparation method of 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid, the steps are as follows:

[0050] (1) Add 2,5-dichlorotoluene (9.34g, 0.058mol), glacial acetic acid (87.08g, 1.45mol), acetic anhydride (88.82g, 0.87mol), concentrated sulfuric acid (46.1g, 0.46mol) in sequence In a 250mL single-necked flask, the reaction system was cooled to 0-5°C in an ice-water bath. Under vigorous stirring, chromium trioxide (29g, 0.29mol) was slowly added in batches, and the addition process continued for 30 minutes. The ice-water bath controlled the reaction temperature at 0-5°C; the final reaction solution continued to stir at this temperature for 2 hours, and then Stir for 24h. The reaction solution was slowly poured into ice water (1700mL), and stirred rapidly, a large amount of light green solid appeared, placed in ultrasonic vibration for 20min, and suction filtered to obtain a light green solid, which was washed in batches with 200mL deionized water, and th...

Embodiment 3

[0055] The preparation method of 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid, the steps are as follows:

[0056] (1) The difference from step (1) of Example 1 is that the amount of chromium trioxide is 23.2g, 0.232mol, and the obtained solid is uniformly dispersed with petroleum ether, and the mixed solution is shaken in an ultrasonic instrument for 1h, and suction filtered to obtain white 19.3 g of solid 2,5-dibromo-diacetoxymethylbenzene, yield 91%.

[0057] (2) The difference from Example 1 step (2) is that the palladium reagent is palladium chloride (71mg, 0.4mmol), the phosphine ligand is tetrakistriphenylphosphine (463mg, 0.8mmol), and the base is trimethylamine ( 6mL), the reaction time was 4h, 1.28g of 2-formyl terephthalic acid was obtained, and the yield was 82%.

[0058] (3) The difference from step (3) of Example 1 is that the palladium reagent is [2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]palladium dichloride (320mg, 0.4mmol ), the phosphine ligand...

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Abstract

The invention discloses a method for synthesizing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid. The synthesis method comprises the following steps: mixing 2,5-dihalotoluene, glacial aceticacid, acetic anhydride and concentrated sulfuric acid, adding chromium trioxide and carrying out an oxidation reaction to obtain 2,5-dihalo-diacetoxymethylbenzene, catalyzing 2,5-dihalo-diacetoxymethylbenzene by a palladium catalyst to obtain 4-halo-3-formylbenzoic acid, and then catalyzing 4-halo-3-formylbenzoic acid by a palladium catalyst to obtain 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid. The preparation method has simple requirements on instruments and equipment, easy availability of raw materials, convenient large-scale preparation, good economic benefits, relatively highproduct yield, and simple reaction post-treatment.

Description

technical field [0001] The invention relates to a method for synthesizing 1-oxo-1,3-dihydro-3-hydroxybenzofuran-5-carboxylic acid, belonging to the field of organic synthesis. Background technique [0002] Terephthalic acid compounds are an important class of dyes, drugs and chemical intermediates. It has potential application value in the 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] In 2014, BaogangWang et al. reported the synthesis of 1-oxo-1,3-dihydrobenzofuran-5-carboxylic acid formic acid containing different substituents at the 3-position, wherein 1-oxo-1,3-dihydro- The yield of 3-hydroxybenzofuran-5-carboxylic acid is 20%, and the synthetic route is as follows: [0004] [0005] In the work ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88
CPCC07D307/88
Inventor 席福贵董智云范建凤赵三虎张佳琪董芝彤
Owner XINZHOU TEACHERS UNIV
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