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

Preparation of 2-alkyl anthracene derivative

A technology of derivatives, alkyl anthracene, applied in the field of preparation of 2-alkyl anthracene derivatives, can solve the problems of high cost and high cost, and achieve the effects of low production cost, low price, and simple and easy separation

Inactive Publication Date: 2009-01-21
HENAN UNIVERSITY
View PDF1 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method utilizes sodium borohydride as a reducing agent, and sodium borohydride is a very expensive reagent, so the cost of this method is higher

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 of 2-alkyl anthracene derivative
  • Preparation of 2-alkyl anthracene derivative
  • Preparation of 2-alkyl anthracene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Dissolve 9.60mmol of anthraquinone in concentrated ammonia water, add 0.19mol of zinc powder and 0.30g of crystalline copper sulfate under stirring, and react at 70-80°C for 2-6 hours to complete the reaction. After cooling to room temperature and filtering, the filtrate was extracted with diethyl ether (3×70 mL), and the filter cake was extracted with diethyl ether (200 mL) by Soxhlet for 3 hours. The ether phases were combined and subjected to silica gel column chromatography to obtain 1.54 g of white product anthracene with a yield of 90.1%.

[0028] The experimental data are as follows: melting point, 212-214°C. 1 H NMR (400MHz, CDCl 3 )δ8.44 (2H, s), 7.90-8.13 (4H, m), 7.39-7.56 (4H, m). MS (EI, 70eV): m / z=178 (100) [M + ]. (Such as figure 1 , figure 2 shown)

[0029] Instrument name and model: TX4-100 micro melting point instrument (the thermometer is not calibrated); Bruker AV-400 nuclear magnetic resonance instrument (CDCl 3 Solvent, internal standard: 7...

Embodiment 2

[0031] Dissolve 9.00mmol of 2-methylanthraquinone in concentrated ammonia water, add 0.18mol of zinc powder and 0.30g of crystalline copper sulfate under stirring, and react at 70-80°C for 2-6 hours to complete the reaction. After cooling to room temperature and filtering, the filtrate was extracted with diethyl ether (3×70 mL), and the filter cake was extracted with diethyl ether (200 mL) by Soxhlet for 3 hours. The ether phases were combined and subjected to silica gel column chromatography to obtain 1.49 g of white product 2-methylanthracene with a yield of 86.1%. The experimental data are as follows: melting point (capillary method) 204-205°C. 1 H NMR (400MHz, CDCl 3 ): δ8.39(1H, s), 8.32(1H, s), 7.96-8.06(2H, m), 7.92(1H, d, J=8.4Hz), 7.76(1H, s), 7.40-7.50( 2H, m), 7.32 (1H, d, J = 8.4Hz), 2.56 (3H, s). MS (EI, 70eV): m / z = 192 (100) [M + ]. (Such as image 3 , Figure 4 shown)

Embodiment 3

[0033] Dissolve 8.46mmol of 2-ethylanthraquinone in concentrated ammonia water, add 0.17mol of zinc powder and 0.30g of crystalline copper sulfate under stirring, and react at 70-80°C for 2-6 hours to complete the reaction. After cooling to room temperature and filtering, the filtrate was extracted with diethyl ether (3×70 mL), and the filter cake was extracted with diethyl ether (200 mL) by Soxhlet for 3 hours. The ether phases were combined and subjected to silica gel column chromatography to obtain 1.02 g of a white product, 2-ethylanthracene, with a yield of 58.3%.

[0034] The experimental data are as follows: melting point (capillary method), 151-152°C. 1 H NMR (400MHz, CDCl 3 )δ8.39(1H, s), 8.35(1H, s), 7.96-8.07(2H, m), 7.94(1H, d, J=8.8Hz), 7.77(1H, s), 7.40-7.51(2H , m), 7.35 (1H, d, J = 8.4Hz), 2.86 (2H, q, J = 7.6Hz), 1.37 (3H, t, J = 7.6Hz). MS (EI, 70eV): m / z =206(100)[M + ], 191(95)[M + -CH 3 ]. (Such as Figure 5 , Figure 6 shown)

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 relates to a preparation method for a 2-alkyl anthracene derivative. The preparation method comprises the following steps that zinc powder is taken as a reducing agent, and crystallized copper sulphate is taken as a catalyst; 2-alkyl substituted anthraquinone reacts inside strong aqua ammonia at a temperature of between 70 and 80 DEG C for 2 to 6 hours; the reaction solution is cooled down to room temperature, and is filtered; the filtrate is extracted 2 to 4 times by diethyl ether, and a filter cake undergoes Soxhlet extraction for 2 to 4 hours by means of diethyl ether; a diethyl ether phase is combined; and finally, the 2-alkyl anthracene derivative can be obtained through silica gel column chromatography. The zinc powder adopted by the preparation method has low price and abundant raw material sources; moreover, the preparation method has the advantages of moderate reaction conditions, simple and easy column chromatography separation, high yield and low cost, and has enormous application value and economic value.

Description

technical field [0001] The invention relates to a preparation method of 2-alkylanthracene derivatives, in particular to a method for synthesizing 2-alkylanthracene from 2-alkylanthraquinone. Background technique [0002] Compared with the price of 2-alkylanthraquinone and 2-alkylanthracene (see Table 1), the price of 2-alkylanthraquinone is much lower than that of 2-alkylanthraquinone. The preparation of expensive alkylanthracene has become the research object of many scholars. U.S. Patent (United States Patent 20030069443) discloses a method for generating 2-alkylanthracene by one-step reduction of 2-alkyl-substituted anthraquinone. The specific technical scheme is: 2-tert-butylanthraquinone is reduced by sodium borohydride 2-tert-butylanthracene is obtained by reducing the agent in isopropanol, and the yield is 50-52% through gas chromatography analysis. This kind method utilizes sodium borohydride as reducing agent, and sodium borohydride is a kind of very expensive rea...

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 Applications(China)
IPC IPC(8): C07C15/28C07C1/207
Inventor 王华赵春梅徐莉
Owner HENAN UNIVERSITY
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