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

Sharing synthesis method for vanillin and isovanillin

A technology for isovanillin and vanillin, which is applied in the field of fragrance and organic intermediate synthesis, can solve the problems of poor reaction selectivity, expensive raw materials, difficult to waste sulfuric acid and the like, and achieves the effects of high yield, simple operation and low environmental pollution.

Inactive Publication Date: 2012-08-01
EAST CHINA UNIV OF SCI & TECH
View PDF6 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this process route is that the raw materials are expensive, the reaction selectivity is poor, and a large amount of waste sulfuric acid that is difficult to handle is produced.

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
  • Sharing synthesis method for vanillin and isovanillin
  • Sharing synthesis method for vanillin and isovanillin
  • Sharing synthesis method for vanillin and isovanillin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Use 1-methoxy-2-isopropoxybenzene 1a as raw material to prepare 3-methoxy-4-isopropoxybenzaldehyde 2a and 3-isopropoxy-4-methoxy Benzaldehyde 3a.

[0042]

[0043] Mix 1-methoxy-2-isopropoxybenzene 1a (20.0g, 0.12mol) and N,N-methylformylaniline (22.0g, 0.16mol), and slowly dissolve oxygen trichloride in an ice-water bath Phosphorus (27.5 g, 0.18 mol) was added dropwise to the above mixture, and after the addition was complete, the reaction was stirred at room temperature to 100° C. and continued to be heated for 20 h. After the reaction, toluene (200 mL) was added for dilution, and then water (100 mL) was added for hydrolysis under an ice-water bath, and stirred for 1 h. The organic layer was separated, washed with 2% sodium hydroxide solution, concentrated and desolvated, and then distilled under reduced pressure to collect the yellow liquid fraction (20.3g, yield 86.9%) at 115-119°C / 2mmHg.

[0044] Spectral data:

[0045] EI-MS (m / z): 194.1 [M + ];

[004...

Embodiment 2

[0064] (1) Use 1-methoxy-2-n-butoxybenzene 1b as raw material to prepare 3-methoxy-4-n-butoxybenzaldehyde 2b and 3-n-butoxy-4-methoxy Benzaldehyde 3b.

[0065]

[0066] Mix 1-methoxy-2-n-butoxybenzene 1b (25.2g, 0.14mol) and N,N-methylformylaniline (25.5g, 0.19mol), and slowly dissolve oxygen trichloride in an ice-water bath Phosphorus (30.6 g, 0.20 mol) was added dropwise to the above mixture, and after the addition was complete, the reaction was stirred at room temperature to 100° C. and continued to be heated for 20 h. After the reaction was completed, toluene (220 mL) was added for dilution, and then water (120 mL) was added for hydrolysis under an ice-water bath, and stirred for 1 h. The organic layer was separated, washed with 2% sodium hydroxide solution, concentrated and desolvated, and then distilled under reduced pressure to collect a yellow liquid fraction (25.1 g, yield 86.2%) at 140-144° C. / 2 mmHg.

[0067] Spectral data:

[0068] EI-MS (m / z): 208.2[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 relates to a sharing synthesis method for vanillin and isovanillin. The method comprises the following steps of: performing alkylation reaction on guaiacol and halogenated hydrocarbon to prepare a 1-methoxy-2-alkoxylbenzene compound 1 in a high-yield way; performing Vilsmeier-Haack reaction on the 1-methoxy-2-alkoxylbenzene compound 1 and N,N-methylformanilide under the action of phosphorus oxychloride to generate a mixture of 3-methoxy-4-alkyloxybenzaldehyde 2 and 3-methoxy-4-methoxybenzaldehyde 3, separating the mixture out, selectively removing alkyl groups by directly using lewis acid to obtain a mixture of vanillin and isovanillin, and separating to prepare two compounds, namely vanillin and isovanillin. The method has the advantages of simplicity and high yield.

Description

【Technical field】 [0001] The invention relates to the technical field of synthesis of spices and organic intermediates, in particular to a process for concurrently synthesizing two important spices, vanillin and isovanillin, and organic synthesis intermediates. 【Background technique】 [0002] In the fragrance industry, vanillin (Scheme 1) is the most used synthetic fragrance, and isovanillin (Scheme 1) is also an important synthetic fragrance. They are the main components of many food flavors and daily flavors. At the same time, vanillin and isovanillin are important synthetic intermediates in the fine organic chemical industry. Starting from them, countless fine chemicals closely related to human life can be synthesized, and they are indispensable in the pharmaceutical and pesticide industries. intermediate. [0003] [0004] Vanillin Isovanillin [0005] Scheme 1 [0006] The industrial preparation method of vanillin mainly adopts the synthetic route (Scheme 2) of ta...

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): C07C47/58C07C47/575C07C45/65
Inventor 冀亚飞黄伟彬卫洁丁涛王树华江健安翟娇娇
Owner EAST CHINA UNIV OF SCI & TECH
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