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A new method for the synthesis of 1,2-dihydrocyclobuteno[α]naphthalene

A dihydrocyclobutene and synthesis method technology, applied in the direction of hydrocarbon production from halogen-containing organic compounds, organic chemistry, etc., can solve the problems of increased production costs, harsh reaction conditions, and low product yields, and achieve low cost and high synthesis The effect of mild conditions and high yield

Active Publication Date: 2016-05-04
绵阳高新区达高特科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] This new synthesis method has harsh reaction conditions, difficult operation, and low product yield, less than 25%, which greatly increases the production cost of the product

Method used

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  • A new method for the synthesis of 1,2-dihydrocyclobuteno[α]naphthalene
  • A new method for the synthesis of 1,2-dihydrocyclobuteno[α]naphthalene

Examples

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Effect test

Embodiment 1

[0055] Weigh 300g of 2-methylnaphthalene, 100g of paraformaldehyde, 250g of glacial acetic acid and 250ml of hydrochloric acid, add them into a 2000ml single-necked round bottom bottle, stir and react at 66°C for 7 hours, analyze the reaction degree of the material by GC, monitor by sampling, and remove the solvent peak , the content of 2-methylnaphthalene is 7.2%, the temperature is lowered to stop the reaction; the reaction solution is poured into 2500ml pre-cooled deionized water, and fully stirred, the water layer is poured off, and then 2500ml of deionized water is added, after fully stirring, discard Remove the water layer, add 2500ml of pre-cooled deionized water again, and discard the water layer to obtain the crude product of 1-chloromethyl-2-methylnaphthalene; add the crude product of 1-chloromethyl-2-methylnaphthalene to a 500ml single-port bottle, and distilled under reduced pressure to remove unconverted raw material 2-methylnaphthalene to obtain high-purity 1-chlo...

Embodiment 2

[0058] Weigh 150g of 2-methylnaphthalene, 55g of paraformaldehyde, 150g of glacial acetic acid and 130ml of hydrochloric acid, add them into a 1000ml single-necked round-bottom bottle, stir and react at 64°C for 8 hours, analyze the reaction degree of the material by GC, monitor by sampling, and remove the solvent peak , the content of 2-methylnaphthalene is 8.2%, the temperature is lowered to stop the reaction; the reaction solution is poured into 1200ml pre-cooled deionized water, and fully stirred, the water layer is poured off, and then 1200ml of deionized water is added, after fully stirring, discard Remove the water layer, add 1200ml of pre-cooled deionized water again, and discard the water layer to obtain the crude product of 1-chloromethyl-2-methylnaphthalene; add the crude product of 1-chloromethyl-2-methylnaphthalene to a 250ml single-port bottle, and distilled under reduced pressure to remove unconverted raw material 2-methylnaphthalene to obtain high-purity 1-chlor...

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Abstract

The invention discloses a novel synthetic method of 1,2-dihydro cyclobutene [alpha] naphthalene, which comprises the following steps that (1) 2-methylnaphthalene, paraformaldehyde, glacial acetic acid and hydrochloric acid are directly fed; heating and reaction are performed at 60-70 DEG C; a 1-chloromethane-2-methylnaphthalene crude product is prepared; (2) the obtained 1-chloromethane-2-methylnaphthalene crude product is subjected to reduced pressure distillation; unconverted 2-methylnaphthalene is removed; high-purity 1-chloromethane-2-methylnaphthalene is obtained; (3) high-purity 1-chloromethane-2-methylnaphthalene is added to a pyrolyzer for pyrolysis; a 1,2-dihydro cyclobutene [alpha] naphthalene crude product is obtained; and (4) the 1,2-dihydro cyclobutene [alpha] naphthalene crude product is dried, distilled, subjected to column chromatography and condensed; and a target product is obtained. Compared with the prior art, the method takes 2-methylnaphthalene as a basic raw material to prepare 1,2-dihydro cyclobutene [alpha] naphthalene by chloromethylation and pyrolysis cyclization, and is mild in synthetic condition, high in yield, very high in production value and good in industrial prospect.

Description

technical field [0001] The invention relates to the production field of pharmaceutical and chemical intermediates, in particular to a new method for synthesizing 1,2-dihydrocyclobuteno[α]naphthalene. Background technique [0002] 1,2-Dihydrocyclobuteno[α]naphthalene has important application value and is widely used in the pharmaceutical industry. The existing method for synthesizing 1,2-dihydrocyclobuteno[α]naphthalene is: The benzene ring reacts with 1-vinylcyclobutene to generate 1,4-dihydronaphtho[α]cyclobutene; 1,4-Dihydronaphtho[α]cyclobutene is further reacted with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form the final product 1,2-dihydro Cyclobuteno[α]naphthalene, the route is as follows: [0003] [0004] This new synthesis method has harsh reaction conditions, high difficulty in operation, and low product yield of less than 25%, which greatly increases the production cost of the product. [0005] The applicant has been engaged in the research on...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/547C07C1/28
Inventor 冯毅汪云峰王超
Owner 绵阳高新区达高特科技有限公司
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