Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of 4-halogenated catechol compound

A technology of halomethylenedioxybenzene and dihalogenation, which is applied in the field of high-purity 4-chloromethylenedioxybenzene and its preparation, and can solve the problems that do not mention 4-chloromethylenedioxybenzene Benzene purity and other issues, to achieve the effect of a simple method

Inactive Publication Date: 2012-02-01
UBE IND LTD
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Moreover, when used as raw materials or synthetic intermediates of medicines and pesticides, it is necessary to use materials that do not substantially contain impurities such as residual raw material methylenedioxybenzene and by-product 4,5-dichloromethylenedioxybenzene. High purity 4-chloromethylenedioxybenzene is evident, but in these documents, there is no mention of the purity of the obtained 4-chloromethylenedioxybenzene

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 4-halogenated catechol compound
  • Preparation method of 4-halogenated catechol compound
  • Preparation method of 4-halogenated catechol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1 (the synthesis of 4-chloromethylenedioxybenzene)

[0056] Into a glass flask with a capacity of 1000 ml equipped with a stirring device, a thermometer and a reflux condenser, under an argon atmosphere, 244.2 g (2.0 mol) of methylenedioxybenzene and 122 g of acetic acid were added, and the temperature of the liquid was raised to 55°C. Then, keeping the liquid temperature at 60-90°C, 216.7 g (1.1 mol) of 1,3-dichloro-5,5-dimethylhydantoin was slowly added, followed by reaction at 70°C with stirring for 1 hour. After the reaction, the reaction solution was cooled to room temperature, 245 ml of hexane and 245 ml of water were added to the reaction solution, stirred, and the organic layer was separated. The obtained organic layer was washed with a 10% aqueous sodium hydroxide solution and a 10% aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and then the concen...

Embodiment 2

[0060] Embodiment 2 (the synthesis of 4-chloromethylenedioxybenzene)

[0061] 1.22 g (10 mmol) of methylenedioxybenzene and 1.22 g of acetic acid were added to a 25 ml glass flask equipped with a stirring device, a thermometer, and a reflux condenser under an argon atmosphere, and the temperature of the liquid was raised to 60°C. Then, keep the liquid temperature at 60-90°C, add 1.13g (5.5mmol) of 1,3-dichloro-5,5-dimethylhydantoin in small amounts each time, and react at 70°C for 1 hour under stirring . After the reaction, the reaction liquid was analyzed by high performance liquid chromatography (absolute quantitative method), and it was revealed that 1.34 g of 4-chloromethylenedioxybenzene was produced (reaction yield: 85.6%).

Embodiment 3

[0064] Embodiment 3 (the synthesis of 4-bromomethylenedioxybenzene)

[0065] 61.1 g (0.5 mol) of methylenedioxybenzene and 30 g of acetic acid were added to a 500-ml glass flask equipped with a stirring device, a thermometer, and a reflux condenser under an argon atmosphere, and the temperature of the liquid was raised to 60°C. Then, keep the liquid temperature at 60-90°C, add 1,3-dibromo-5,5-dimethylhydantoin 78.6g (0.275mol) in small amounts each time, and react at 70°C for 1 hour under stirring . After the reaction, the reaction solution was cooled to room temperature, and 200 g (1.0 mol) of 20% aqueous sodium hydroxide solution was added to the reaction solution, followed by stirring. Then, the reaction liquid was filtered, and the organic layer was separated, and then the organic layer was distilled under reduced pressure (93° C., 1200 Pa) to obtain 71.2 g of 4-bromomethylenedioxybenzene as a colorless liquid (isolation yield: 70.8%).

[0066] The physical property para...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Disclosed is a method for producing a 4-halocatechol compound, which is characterized in that a catechol compound is reacted with 1,3-dihalo-5,5-dimethylhydantoin. Also disclosed are a high-purity 4-chloromethylenedioxybenzene which is characterized in that the methylenedioxybenzene content is not more than 0.5% by mass and the 4,5-dichloromethylenedioxybenzene content is not more than 0.5% by mass, and a method for producing such a high-purity 4-chloromethylenedioxybenzene.

Description

technical field [0001] The present invention relates to a new preparation method of 4-halogenated catechol compounds. The 4-halogenated catechol compounds can be used as raw materials or synthetic intermediates of medicines and pesticides. [0002] The invention also relates to high-purity 4-chloromethylenedioxybenzene and a preparation method thereof. High-purity 4-chloromethylenedioxybenzene can be used as raw materials or synthetic intermediates for medicines and pesticides. Background technique [0003] At present, the methods for preparing 4-halogenated catechol compounds such as 4-chloromethylenedioxybenzene from catechol compounds have been disclosed, such as the following methods: [0004] (1) In the presence of sulfonyl chloride, react benzodioxol, aluminum trichloride and diphenylsulfide to prepare 5-chloro-1,3-benzodioxol Alkenes (see, for example, Patent Document 1). [0005] (2) A method of preparing 1-chloro-3,4-methylenedioxybenzene by reacting 1,2-methyle...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/22C07C43/225C07D317/62
CPCC07C41/22C07D317/62C07C43/225
Inventor 西野繁栄中村明小田広行小俣洋治
Owner UBE IND LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com