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Synthesis method of 1-pyrenol and intermediates thereof

A synthesis method and a technology for hydroxypyrene are applied in chemical instruments and methods, preparation of carbonyl compounds by condensation, preparation of organic compounds, etc., and can solve problems such as difficulty in demethylation, difficulty in industrialization, high price of 1-bromopyrene, and the like, To achieve the effect of easy operation, saving production cost and less pollution

Active Publication Date: 2016-07-06
YURUI SHANGHAI CHEM
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Problems solved by technology

[0006] The shortcoming of this method is: to use the quite serious chlorosulfonic acid of environmental pollution, also have the temperature of alkaline hydrolysis to need more than 260 ℃, be difficult to industrialization
[0009] The shortcoming of this method is: raw material 1-bromopyrene is expensive; simultaneously in the demethylation process owing to not having found a good demethylation reagent at present, so be difficult to realize demethylation

Method used

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  • Synthesis method of 1-pyrenol and intermediates thereof
  • Synthesis method of 1-pyrenol and intermediates thereof
  • Synthesis method of 1-pyrenol and intermediates thereof

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Embodiment 1

[0031] Embodiment 1, the synthetic method of a kind of 1-hydroxypyrene of the present invention and its intermediate comprises the following steps:

[0032] Step 1, utilizing the Friedel-Crafts acylation reaction of pyrene and acetyl chloride to prepare the intermediate acetylpyrene;

[0033] Step 2, using the bayer-villiger oxidative rearrangement reaction (Baeyer-Villiger oxidation rearrangement reaction, Bayer-Villiger oxidative rearrangement reaction is an oxidation reaction in which peroxyacid oxidizes ketones into esters, and occurs in the reaction Nucleophilic rearrangement, commonly used peroxyacids in the reaction are peroxyacetic acid, peroxytrifluoroacetic acid, peroxybenzoic acid, 3-chloroperoxybenzoic acid, peroxysulfuric acid, etc.), to prepare the intermediate acetoxypyrene ;

[0034] Step 3, preparing 1-hydroxypyrene by saponification reaction.

[0035] The detailed steps are as follows:

[0036] Synthesis of intermediate 1-acetylpyrene, add 202g of pyrene (...

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Abstract

The invention discloses a synthesis method of 1-pyrenol and intermediates thereof.The synthesis method includes firstly, preparing an intermediate, namely acetylpyrene by subjecting pyrene and acetyl chloride to Friedel-Crafts reaction; secondly, preparing an intermediate, namely acetoxypyrene by Baeyer-Villiger oxidation rearrangement; thirdly, preparing the 1-pyrenol by saponification.The synthesis method has the advantages that the 1-pyrenol and the intermediates thereof are prepared from the pyrene and the acetyl chloride, and accordingly the synthesis method is economic, easy to operate, little in environmental pollution, capable of saving production cost for enterprises and high in reaction yield rate of the 1-pyrenol and the intermediates thereof.

Description

technical field [0001] The invention relates to a method for synthesizing organic matter, in particular to a method for synthesizing 1-hydroxypyrene and its intermediates. Background technique [0002] As an important derivative of pyrene, 1-hydroxypyrene is a product of pyrene's metabolism in vivo. 1-hydroxypyrene in urine is a sensitive indicator of human exposure to polycyclic aromatic hydrocarbons, and has increasingly attracted the attention of researchers. [0003] There are two commonly used synthesis methods: [0004] Method one, adopt chlorosulfonic acid to alkali hydrolysis at high temperature, its chemical reaction formula is as follows: [0005] [0006] The shortcoming of this method is: will use the quite serious chlorosulfonic acid of environmental pollution, also have the temperature of alkaline hydrolysis to need more than 260 ℃, be difficult to industrialization. At the same time, because the temperature is too high, 1-hydroxypyrene is easily oxidized,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/12C07C37/055C07C67/42C07C69/157C07C45/46C07C49/788
CPCC07C37/0555C07C45/46C07C67/42C07C39/12C07C69/157C07C49/788
Inventor 韩爱英赵晓宇宋文志吴跃初
Owner YURUI SHANGHAI CHEM
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