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Microwave synthesis method of three asymmetric porphyrins

A microwave synthesis and asymmetric technology, applied in the direction of organic chemistry, can solve the problems of reduced yield, increased by-products, difficult separation and purification of products, etc., to achieve the effects of reduced by-products, high product purity, and improved yield

Inactive Publication Date: 2013-03-06
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Porphyrin compounds are generally synthesized by conventional heating methods, and the reaction time is relatively long (about 2 hours). Pyrrole and aldehydes are prone to reactions such as oxidation and polymerization during the long-term heating process, and the by-products increase, making it difficult to separate and purify the product and reduce the yield. Asymmetric porphyrins also reduce the yield of target porphyrins due to the increase of by-products

Method used

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  • Microwave synthesis method of three asymmetric porphyrins
  • Microwave synthesis method of three asymmetric porphyrins
  • Microwave synthesis method of three asymmetric porphyrins

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Embodiment 1

[0026] Weigh 4-hydroxybenzaldehyde (25mmol, 3.05g) in a three-necked flask, measure 60ml of propionic acid to dissolve, place a temperature probe and a condenser tube, fix it in a microwave instrument, set the target temperature to 142°C and the power (to reach the target temperature Time) 10min, start stirring and heating work. Measure a solution of pyrrole (25mmol, 1.75ml) dissolved in 15ml of propionic acid. After reflux, the dropwise addition is completed within 2 minutes, and the microwave reaction is continued for 20 minutes. After the reaction was completed, cool to room temperature, evaporate nearly half of the solvent under reduced pressure, and refrigerate overnight. Suction filtration to obtain a purple-black solid, chloroform was used as eluent, silica gel column chromatography, the first purple-red color band was collected, and vacuum-dried to obtain a blue solid, which was then washed with ethyl acetate-petroleum ether (2:1, V:V) Recrystallization gave 1.04 g of...

Embodiment 2

[0028] Dissolve 3.40ml (25mmol) of 1-naphthaldehyde and 1.02g (8.3mmol) of m-hydroxybenzaldehyde in 60ml of propionic acid, heat in microwave to reflux, and add dropwise 2.30ml (33mmol) of pyrrole dissolved in 15ml of propionic acid within 2 minutes. Solution, continue microwave reaction for 20 minutes under the microwave power of 10 minutes. After the reaction was completed, cool to room temperature, evaporate nearly half of the solvent under reduced pressure, add an equal amount of methanol to the remaining mother liquor, and refrigerate overnight. Suction filtration gave a purple-black solid, and the crude product was dichloromethane-petroleum ether (3:1, V: V) Carry out column chromatography as the eluent, collect the purple-red second color band, dry in vacuo to obtain a blue-purple solid, and then recrystallize with ethyl acetate-petroleum ether (2:1, V:V) to obtain a blue-purple crystal, That is, 0.67 g of 5-m-hydroxyphenyl-10,15,20-trinaphthylporphyrin (1), the yield i...

Embodiment 3

[0030] Dissolve 3.40ml (25mmol) of 1-naphthaldehyde and 1.28g (8.3mmol) of 3-hydroxy-4-methoxybenzaldehyde in 60ml of propionic acid, heat to reflux in microwave, and add 2.30ml (33mmol) dropwise within 2 minutes Pyrrole was dissolved in a solution of 15ml propionic acid, and the microwave reaction was continued for 20 minutes under the microwave power of 10 minutes. After the reaction was completed, cool to room temperature, evaporate nearly half of the solvent under reduced pressure, add an equal amount of methanol to the remaining mother liquor, and refrigerate overnight. Suction filtration gave a purple-black solid, and the obtained crude product was dichloromethane-petroleum ether (3:1 , V:V) as the eluent for column chromatography, collecting the purple-red second color band, drying in vacuo to obtain a blue-purple solid, and then recrystallizing with ethyl acetate-petroleum ether (2:1, V:V) to obtain a blue Purple crystal, 5-(3-hydroxy-4-methoxy)phenyl-10,15,20-trinapht...

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Abstract

The invention discloses a microwave synthesis method of three new asymmetric porphyrins and optimized conditions for porphyrin synthesis. The method comprises the following steps: carrying out microwave synthesis by using p-hydroxybenzaldehyde as a substrate to obtain meso-tetra(4-hydroxyphenyl)porphyrin, wherein the yield reaches the maximum when the reaction is carried out for 20 minutes under the 10-minute microwave power; under such optimized conditions, synthesizing the three new asymmetric porphyrins, namely 5-m-hydroxyphenyl-10,15,20-trinaphthylporphyrin, 5-(3--hydroxy-4-methoxy)phenyl-10,15,20-trinaphthylporphyrin and 5-p-dimethylaminophenyl-10,15,20-trinaphthylporphyrin; and by using an improved the Adler process, synthesizing the acid-sensitive 5-p-dimethylaminophenyl-10,15,20-trinaphthylporphyrin by a propanoic acid-glacial acetic acid-nitrobenzene mixed-solvent process. Compared with the conventional heating process for synthesizing porphyrins, the method disclosed by the invention can greatly shorten the reaction time, reduce the byproducts, enhance the yield to some extent, and have the advantage of energy saving, environmental protection and the like, thereby conforming to green chemical engineering.

Description

technical field [0001] The invention discloses a method for synthesizing asymmetric porphyrin by microwave, and also discloses an optimized condition and a purification method for synthesizing porphyrin by microwave method. Background technique [0002] Porphyrin is a general term for a class of macrocyclic compounds with a porphine nucleus. It occupies an important position in the research of biochemistry, medicine, coordination chemistry, analytical chemistry, electrochemistry, photochemistry and catalysis. [0003] The synthesis of porphyrins has always been a hot topic of research, mainly due to the low yield of porphyrin compounds and the difficulty of separation and purification. As early as more than 60 years ago, P. Rothemund et al. synthesized tetraphenylporphyrin for the first time in a sealed tube using pyridine as a solvent. In 1964, Adler studied the influence of different solvents, metal cations, reaction temperature and time on the polycondensation reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
Inventor 俞善辉戴聪聪
Owner EAST CHINA UNIV OF SCI & TECH
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