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

Synthesis method of triarylmethane and derivative thereof under solvent-free condition

An arylmethane and a synthesis method technology, applied in the field of organic compound synthesis, can solve problems such as high cost and inability to recover, and achieve the effects of small environmental impact, cheap raw material range and good universality

Inactive Publication Date: 2018-02-09
HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the cost is expensive, and there are certain limitations, and good yields can only be achieved for some compounds
Ferric chloride has also been used as a catalyst for the synthesis of triarylmethane, but it needs the assistance of acetic anhydride and cannot be recycled, and it also has certain limitations.

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
  • Synthesis method of triarylmethane and derivative thereof under solvent-free condition
  • Synthesis method of triarylmethane and derivative thereof under solvent-free condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1.5, the synthesis of 5'-(benzyl) bi-(2-methylfuran):

[0017] Add 1mmol (0.103mL) benzaldehyde, 2mL 2-methylfuran, and 0.1mmol sulfamic acid into a round bottom flask, then heat to 70°C with an oil bath under magnetic stirring, and react for 6 hours. Remove the oil bath and cool down to room temperature; the catalyst is filtered out, the mother liquor is concentrated by a rotary evaporator, and the residue is separated by silica gel thin-layer chromatography using petroleum ether as a developing solvent. Pure triarylmethane was obtained with an isolated yield of 90.0%. The nuclear magnetic analysis data of this compound are as follows:

[0018] 1 H NMR (400MHz, CDCl 3 )δ:7.31-7.21(m,5H),5.87-5.85(m,4H),5.33(s,1H),2.23(s,6H). 13 C NMR (100MHz, CDCl 3 )δ: 152.8, 151.4, 140.0, 128.4, 128.3, 126.9, 108.1, 106.0, 45.1, 13.6. MS: m / z 252.10 [M] + ..

Embodiment 2

[0019] Embodiment 2.5, the synthesis of 5'-(p-methylbenzyl) bi-(2-methylfuran):

[0020] Add 1mmol (0.103mL) p-tolualdehyde, 2mL 2-methylfuran, 0.1mmol sulfamic acid into a round bottom flask, then heat to 80°C with an oil bath under magnetic stirring, and react for 6 hours. Remove the oil bath and cool down to room temperature; the catalyst is filtered out, the mother liquor is concentrated by a rotary evaporator, and the residue is separated by silica gel thin-layer chromatography using petroleum ether as a developing solvent. Pure triarylmethane was obtained with an isolated yield of 98%. The nuclear magnetic analysis data of this compound are as follows:

[0021] 1 H NMR (400MHz, CDCl 3 )δ:7.15-7.09(m,4H),5.86-5.84(m,4H),5.29(s,1H),2.30(s,3H),2.22(s,6H). 13 C NMR (100MHz, CDCl 3 )δ: 153.0, 151.3, 137.0, 136.4, 129.1, 128.2, 108.0, 106.0, 44.7, 21.0, 13.6. MS: m / z 266.10[M] + ..

Embodiment 3

[0022] Embodiment 3.5, the synthesis of 5'-(p-bromobenzyl) bi-(2-methylfuran):

[0023] Add 1mmol (0.103mL) of p-bromobenzaldehyde, 2mL of 2-methylfuran, and 0.1mmol of sulfamic acid into a round-bottomed flask, then heat to 90°C with an oil bath under magnetic stirring, and react for 6 hours. Remove the oil bath and cool down to room temperature; the catalyst is filtered out, the mother liquor is concentrated by a rotary evaporator, and the residue is separated by silica gel thin-layer chromatography using petroleum ether as a developing solvent. Pure triarylmethane was obtained with an isolated yield of 91.2%. The nuclear magnetic analysis data of this compound are as follows:

[0024] 1 H NMR (400MHz, CDCl 3 )δ: 7.41(d, J=8.4Hz, 2H), 7.11(d, J=8.4Hz, 2H), 5.87-5.86(m, 4H), 5.28(s, 1H), 2.23(s, 6H). 13 C NMR (100MHz, CDCl 3 )δ: 152.1, 151.6, 139.0, 131.5, 130.1, 120.8, 108.3, 106.1, 44.5, 13.6. MS: m / z 330.00, 332.00 [M] + ..

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 synthesis method of triarylmethane and a derivative thereof under a solvent-free condition and belongs to the field of synthesis of organic compounds. According to the synthesis method disclosed by the invention, sulfamic acid is used as a catalyst and aromatic aldehyde and aromatic hydrocarbon are used as raw materials to synthesize a target object through one-step synthesis. The synthesis method disclosed by the invention has moderate reaction conditions, the catalyst is environmentally friendly and can be recycled and the yield is high; the low yield reaches 43 percent or more and the high yield reaches 98 percent or more; the synthesis method has relatively good universality, small influences on environment and actual popularization and application value.

Description

technical field [0001] The field of the invention relates to a synthesis method of organic compounds, and relates to a new synthesis method of triarylmethane and its derivatives. Background technique [0002] Triarylmethane and its derivatives play an important role in materials, medicine, dyes, chemical industry and other fields. And triarylmethane derivatives are very useful protecting groups, which are applied in many chemical synthesis and can also be used as optical reagents. [0003] At present, most of the methods for synthesizing triarylmethanes require complex processes and harsh conditions, such as documents K.Fukui, Y.Inamoto, H.Kitano and C.Nagata, J.Am.Chem.Soc., 1959,81,5954 ; E.F.Prattand L.Q.Green, J.Am.Chem.Soc., 1949, 71, 275; C.G.Ekstrom, Acta.Chem.Scand., 1966, 20, 444; C.D.Ritche, W.F.Sager and E.S.Lewis, J.Am.Chem.Soc. , 1962, 84, 2349; Z-H Zhang, F. Yang, T-S Li and C-G Fu, Synth. Commun., 1997, 27, 3823; P. Shanmuga and L. Varma, Ind. J. Chem. 2001,...

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): C07D307/36C07D307/38C07D307/52C07D307/42C07D333/08C07F5/02C07C41/30C07C43/205
CPCY02P20/584C07D307/36C07C41/30C07D307/38C07D307/42C07D307/52C07D333/08C07F5/025C07C43/2055
Inventor 李中贤刘小培李玉江王俊伟董学亮余学军
Owner HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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