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

Method for synthesizing 3-hydroxy biphenyl

A technology of hydroxybiphenyl and synthesis method, which is applied in chemical instruments and methods, magnesium organic compounds, preparation of organic compounds, etc., can solve the problems of cumbersome processing, high cost, expensive, etc., and meet the requirements of simple reaction equipment and easy control of reaction , the effect of mild reaction conditions

Inactive Publication Date: 2019-05-24
SHANGHAI JINGCHUN BIOCHEM TECH CO LTD
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthetic research of 3-hydroxybiphenyl has been reported in many domestic and foreign literatures, generally using Suzuki coupling reaction, that is, in alkali (K 2 CO 3 、K 3 PO 4 , NaOH, etc.) under the action of palladium catalysis (Pd(PPh 3 ) 4 or PdCl 2 (PPh 3 ) 2 ) of organic aromatic borides (3-hydroxyphenylboronic acid or phenylboronic acid) and halogenated aromatic benzenes (bromobenzene or 3-bromophenol) and other cross-coupling reactions to synthesize 3-hydroxybiphenyls, but there is a problem, The post-reaction treatment is cumbersome, and the product purification is difficult. The most important thing is that the expensive metal palladium catalyst is used, which is costly and not suitable for industrial production.

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
  • Method for synthesizing 3-hydroxy biphenyl
  • Method for synthesizing 3-hydroxy biphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] This embodiment provides a process for synthesizing 3-hydroxybiphenyl, and the specific synthesis steps are as follows:

[0031] (1) prepare 10L glass reactor, N 2 protection, adding magnesium scraps (171g, 7.12mol) and 800ml solvent THF in sequence, then heating to 62-64°C, adding dropwise a THF (2L) solution of 3-bromoanisole (1.27kg, 6.78mol) to keep a slight Add dropwise under boiling conditions. After the dropwise addition, mature at 62-65°C for 1 hour to react 3-bromoanisole with magnesium chips to obtain Grignard reagent;

[0032] (2) Cool the Grignard reagent prepared in step (1) to 5-10°C in an ice-water bath, and then add the catalyst dpppNiCl first 2 (3.5g, 6.45mmol), then add bromobenzene (845g, 5.38mol) dropwise, the rate of addition is controlled within 1.0-1.5h, after the dropwise addition, first react at an internal temperature of 40°C for 1h, then reflux at 68°C for 3h; After the reaction, cool the reaction solution to 5-10°C, add 600ml concentrated h...

Embodiment 2

[0040] This embodiment provides a process for synthesizing 3-hydroxybiphenyl, and the specific synthesis steps are as follows:

[0041] (1) prepare 10L glass reactor, N 2 protection, adding magnesium chips (179g, 7.46mol) and 800ml solvent THF in sequence, then heating to 62-64°C, adding dropwise a THF (2L) solution of 3-bromoanisole (1.27kg, 6.78mol) to keep a slight Add dropwise under boiling conditions. After the dropwise addition, mature at 62-65°C for 1 hour to react 3-bromoanisole with magnesium chips to obtain Grignard reagent;

[0042] (2) Cool the Grignard reagent prepared in step (1) to 5-10°C in an ice-water bath, and then add the catalyst dpppNiCl first 2 (3.5g, 6.45mmol), then added dropwise bromobenzene (1064g, 6.78mol), the rate of addition was controlled within 1.5-2.0h, after the dropwise addition, the internal temperature was first reacted at 40°C for 1h, and then refluxed at 68°C for 3h; After the end, cool the reaction solution to 5-10°C, add 600ml concen...

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

The invention discloses a method for synthesizing 3-hydroxy biphenyl, which is characterized by comprising the following steps of: under the protection of inert gas or N2 gas, using THF as a solvent,reacting bromoanisole with magnesium scraps to obtain a Grignard reagent; reacting Grignard reagent with bromobenzene in the presence of a catalyst dpppNiCl2, adding an acid solution for quenching reaction, layering, extracting water phase, separating liquid, combining the obtained organic phases, washing, drying, concentrating, and distilling to obtain an intermediate 3-methoxybiphenyl; adding the 3-methoxybiphenyl into glacial acetic acid, adding a 48% HBr solution, heating, refluxing, aging, cooling, extracting and separating, mixing the obtained organic phases, washing, drying, concentrating, and recrystallizing toluene to obtain the 3-hydroxy biphenyl. The method has the advantages of convenient operation, easy control of reaction and simple requirement on reaction equipment, the whole process is suitable for industrial production, and the GC purity of the prepared 3-hydroxy biphenyl can reach more than 99%, and the total yield is more than 60%.

Description

technical field [0001] The invention relates to a method for high-purity 3-hydroxybiphenyl, which belongs to the technical field of synthesis of new organic materials and application of pharmaceutical intermediates. Background technique [0002] 3-Hydroxybiphenyl is an important fine organic chemical product and organic intermediate. It has a wide range of uses including food antiseptic and sterilization, synthesis of printing and dyeing auxiliaries, synthesis of heat-stable materials, preparation of new flame retardants, etc., as well as application in the development and research of new pharmaceuticals middle. In recent years, with the continuous development of economy and science and technology, the market demand for 3-hydroxybiphenyl has increased year by year. Therefore, it is very important to develop a method for synthesizing high-purity 3-hydroxybiphenyl and realizing industrialization. [0003] The synthetic research of 3-hydroxybiphenyl has been reported in many ...

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
IPC IPC(8): C07C39/15C07C37/055C07F3/02C07C43/205C07C41/30
Inventor 阚洪柱姜苏徐久振
Owner SHANGHAI JINGCHUN BIOCHEM TECH CO 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