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

Method for preparing 6-methoxyl-2-naphthaldehyde

A technology of methoxyl and naphthalene formaldehyde, applied in the field of preparation of 6-methoxy-2-naphthalene formaldehyde, can solve problems such as long route and reduced production cost, and achieve the effects of reducing production cost and reducing discharge of industrial wastes

Inactive Publication Date: 2015-03-25
ZHEJIANG TIANXIN PHARMA
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The improved method solves the problems of inorganic salts in the original method, but still uses highly toxic dimethyl sulfate as raw material, and the route is long, which is not conducive to the reduction of production costs

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

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0015] The invention provides a kind of preparation method of 6-methoxy-2-naphthaldehyde, the method comprises the following steps:

[0016] (1) Contact 6-methoxy-2-naphthoic acid with alcohol for esterification to obtain 6-methoxy-2-naphthoate;

[0017] (2) contacting the 6-methoxy-2-naphthoate obtained in step (1) with a reducing agent to perform a reduction reaction to obtain 6-methoxy-2-naphthylmethanol;

[0018] (3) Contacting the 6-methoxy-2-naphthylmethanol obtained in step (2) with an oxidizing agent to carry out an oxidation reaction to obtain 6-methoxy-2-naphthaldehyde.

[0019] Preferably, according to the preparation method of the present invention, in step (1), the mass ratio of the 6-methoxy-2-naphthoic acid to alcohol may be 1:1-20, wherein, when the When the mass ratio of 6-methoxyl group-2-naphthoic acid and alcohol is 1:1-3, described alcohol can be used as raw material in esterification reaction with other solvents that can be used for esterification reacti...

Embodiment 1

[0046] This example is used to illustrate the preparation method of 6-methoxy-2-naphthaldehyde.

[0047] (1) Preparation of 6-methoxy-2-naphthyl methyl ester

[0048] Put 20.0 g of 6-methoxy-2-naphthoic acid and 200 g of methanol into a three-necked flask, add 1 g of concentrated sulfuric acid with a mass fraction of 98%, stir and heat up to reflux, and react for 12 hours. After the reaction was finished, approximately 120 g of methanol was recovered by atmospheric distillation, and crystals were precipitated after the residual liquid was cooled to 0 ° C. After filtration, the mother liquor was recovered and the filter residue was washed with methanol, and dried to obtain 20.50 g of 6-methoxy-2-naphthyl methyl ester, with a melting point of 129.5-130.2°C, the purity is 99.23% by HPLC. 0.45 g of 6-methoxy-2-naphthyl methyl ester was recovered from the mother liquor, and its purity by HPLC was 95.2%, and the total yield was 98.0%.

[0049] Detect gained 6-methoxy-2-naphthyl me...

Embodiment 2

[0057] This example is used to illustrate the preparation method of 6-methoxy-2-naphthaldehyde.

[0058] (1) Preparation of 6-methoxy-2-naphthyl methyl ester

[0059] Put 40.0 g of 6-methoxy-2-naphthoic acid and 600 g of methanol into a three-necked flask, add 6 g of concentrated sulfuric acid with a concentration of 98% by mass, stir and heat up to reflux, and react for 8 hours. After the reaction was completed, 480 g of methanol was recovered by atmospheric distillation, and the remaining reaction solution was cooled to 20°C for crystallization, filtered, washed with methanol, and dried to obtain 41.22 g of 6-methoxy-2-naphthyl methyl ester with a melting point of 129.3 to 130.1 ℃, and its purity was 99.34% by HPLC. 0.97 g of 6-methoxy-2-naphthyl methyl ester was recovered from the mother liquor, and its purity was 94.7% as detected by HPLC. The total yield is 98.6%.

[0060] (2) Preparation of 6-methoxy-2-naphthylmethanol

[0061]Put 114.3g of bis(2-methoxyethoxy)sodium...

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 preparing 6-methoxyl-2-naphthaldehyde. The method comprises the following steps: (1) contacting 6-methoxyl-2-naphthoic acid with alcohol to obtain 6-methoxyl-2-naphthoate through esterification reaction; (2) contacting the 6-methoxyl-2-naphthoate resulting from step (1) with a reducing agent to acquire 6-methoxyl-2-naphthalene methanol through reduction reaction; (3) contacting the 6-methoxyl-2-naphthalene methanol resulting from step (2) with an oxidizing agent to obtain 6-methoxyl-2-naphthaldehyde through oxidation reaction. According to the invention, the method has advantages of less discharge of industrial waste, low production cost and being environment-friendly and safe.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a preparation method of 6-methoxy-2-naphthaldehyde. Background technique [0002] Nabumetone is a long-acting non-steroidal anti-inflammatory analgesic, clinically used to treat various acute / chronic inflammatory arthritis, rheumatoid arthritis, ankylosing spondylitis, osteoarthritis, gouty diseases such as arthritis. The efficacy of nabumetone is similar to that of naproxen, but it has much less gastrointestinal side effects than napropionate NSAIDs and is well tolerated, so it has become the most widely used NSAID at present. One of the body anti-inflammatory drugs. 6-Methoxy-2-naphthaldehyde is a key intermediate in the synthesis of nabumetone, so the research on its synthesis method has also aroused widespread concern. [0003] Fangzheng et al. (Journal of China Pharmaceutical University, 35(1): 90-91) improved on the basis of the literature, using β-naphthyl methyl ether ...

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): C07C47/575C07C45/29
CPCC07C45/298C07C41/26C07C67/08C07C47/575C07C43/23C07C69/92
Inventor 徐勇智董新电章根宝范卫东张平向晶凌海源
Owner ZHEJIANG TIANXIN PHARMA
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