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

Preparation method of hydroxymethyl substitutent o-alkyl biphenyl and intermediate thereof

A technology of alkyl biphenyl and hydroxymethyl, applied in the field of preparation of hydroxymethyl substituted o-alkyl biphenyl and its intermediates, can solve the problems of long route, high production cost, lack of

Inactive Publication Date: 2010-05-12
JIANGSU WEIER CHEM +1
View PDF2 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has a long route, high raw material prices, and strict anhydrous operation, resulting in high production costs
According to the above method, it is unfavorable for industrialized production, so that there are many difficulties in industrial realization
[0005] In summary, the art lacks a process route for directly obtaining halogenated o-alkylbiphenyls from halogenated o-alkylanilines, but first obtains dihaloalkylbenzenes, and then obtains halogenated o-alkylbiphenyls

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 hydroxymethyl substitutent o-alkyl biphenyl and intermediate thereof
  • Preparation method of hydroxymethyl substitutent o-alkyl biphenyl and intermediate thereof
  • Preparation method of hydroxymethyl substitutent o-alkyl biphenyl and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0098] The preparation method of halogenated o-alkyl biphenyl intermediate of the present invention comprises the steps:

[0099] (a) providing the halogenated o-alkylaniline shown in formula (I) as raw material:

[0100]

[0101] where R is C n h 2n+1 , n=1, 2, 3, 4, or 5;

[0102] X is F, Cl, Br, or I;

[0103] (b) In the presence of metal catalysts, acid cocatalysts and nitrite esters, the halogenated o-alkylanilines of the formula (I) of step (a) carry out diazo coupling reactions with benzene to obtain formula (II) ) of halogenated o-alkylbiphenyl compounds:

[0104]

[0105] Wherein R and X in formula (II) have the same meanings as formula (I).

[0106] In the above diazo coupling reaction, the amino group in the compound of formula (I) is coupled by diazo to obtain the compound of formula (II).

[0107] In a preferred example, the halogenated o-alkylaniline of the formula (I) is 3-chloro-2-methylaniline; the halogenated o-alkylbiphenyl compound of the formul...

Embodiment 1

[0152] Put 3-chloro-2-methylaniline (71g, 0.5mol) and benzene (300ml, 3.38mol) into a 1000ml four-necked flask, and start stirring. Ferric chloride (2g, 0.012mol), triethyl orthoformate Ester (55g, 0.34mol) was put into the reactor. The oil bath controlled the reaction temperature at 40°C, and isopropyl nitrite (80g, 0.9mol) and benzene (200mL, 2.25mol) were added to the constant pressure dropping funnel , under the condition of maintaining a constant reaction temperature of 40°C, drop it into the reactor. After the dropwise addition of isopropyl nitrite, stir at 40°C for 2 hours. Cool down to room temperature, drop in urea (50g) and 30% hydrochloric acid (200g) After phase separation, the organic layer was rectified. Recover benzene first, and then continue rectifying to obtain the refined product 3-chloro-2-methylbiphenyl (76g, 0.37mol). The gas chromatography analysis purity is 99.5%, and the yield is 75%.

Embodiment 2～ Embodiment 9

[0154] Metal catalyst consumption or kind are changed, and other is with embodiment 1, and its result is shown in Table 1

[0155] Table 1

[0156] implement

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 provides a preparation method of hydroxymethyl substitutent o-alkyl biphenyl and intermediate thereof, which takes halogen o-alkyl biphenyl as a raw material to synthesize halogen o-alkyl biphenyl through diazonium coupling reaction. The raw materials and catalyst utilized by the invention are massively commercialized at home and abroad and all around the world with low price. The method of the invention has low production cost, short synthetic route, mild reaction condition, easy and feasible operation process, less three wastes (waste gas, waste water and industrial residue) generation, low cost of raw materials and high yield and purity, thereby being favorable to industrial volume production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of hydroxymethyl-substituted o-alkyl biphenyls and intermediates thereof. Background technique [0002] Among the hydroxymethyl-substituted o-alkyl biphenyl compounds, the more important one is 2-methyl-3-phenylbenzyl alcohol, which is mainly used in the production of the pesticide bifenthrin and as a raw material for the synthesis of other pharmaceutical products. [0003] Chinese patent applications CN200610096552.2 and CN200710130941.7 describe methods for preparing 2-methyl-3-phenylbenzyl alcohol. Among them, the preparation method of the halogenated o-alkyl biphenyl intermediate is as follows: using dihalogenated alkylbenzene as a raw material, after Grignard reaction in the solvent tetrahydrofuran, it is coupled with brominated benzene to obtain the halogenated o-alkyl biphenyl . Grignard reaction and reduction reaction are then c...

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): C07C33/24C07C29/14C07C25/18C07C17/263C07C47/546C07C45/00
Inventor 谈平忠袁明
Owner JIANGSU WEIER CHEM
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