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

Synthesis method of 5-methoxy-2-tetralone

A synthetic method and technology of tetralone, which is applied in the field of synthesis of 5-methoxy-2-tetralone, can solve the problems that the use of sodium is easily affected by environmental humidity, unfavorable for safe production, and expensive synthetic raw materials, etc. Short steps, easy operation, less three waste pollutants

Pending Publication Date: 2021-08-10
WUHAN INSTITUTE OF TECHNOLOGY
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the existing synthetic method of rotigotine hydrochloride intermediate 5-methoxy-2-tetralone, 1,6-dihydroxynaphthalene is used as raw material to react with dimethyl sulfate, which is highly toxic substances and the reaction will produce a large amount of sulfur dioxide, which is dangerous for the operator; the product undergoes a reduction reaction with metallic sodium, and metallic sodium is an explosive-prone item that is not conducive to safe production, and the use of sodium is easily affected by environmental humidity; finally, with Hydrochloric acid reaction to get 5-methoxy-2-tetralone
This route has the problems of expensive synthetic raw materials and complex synthetic routes

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 5-methoxy-2-tetralone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 1.66g (10mmol) 3-methoxyphenylacetic acid and magneton into a 50mL three-necked flask, install a condenser tube and a dropping funnel, place the instrument in an oil bath, set the temperature to 55°C, and turn on the stirring and condenser tube , then add 10mL of thionyl chloride and 0.5mL of N,N-dimethylformamide into the dropping funnel, wait until the temperature rises to 55°C, start the dropwise addition, and slowly add the solution into the reactor at a rate of 0.1mL / s, after the dropwise addition is completed, reset the heating temperature to 90°C, stir for 3 hours, and use TLC to confirm that the reaction is complete and prepare to start purification.

[0034] After the liquid in the reactor was cooled to room temperature, it was taken out in an eggplant-shaped bottle, and the contents of the eggplant-shaped bottle were rotated under reduced pressure at 60°C to remove excess thionyl chloride. After the rotary evaporation was completed, 30 mL of n-hexane was a...

Embodiment 2

[0039] Add 1.66g (10mmol) 3-methoxyphenylacetic acid and magneton into a 50mL three-necked flask, install a condenser tube and a dropping funnel, place the instrument in an oil bath, set the temperature to 55°C, and turn on the stirring and condenser tube , and then add 10mL of thionyl chloride and 0.5mL of N,N-dimethylformamide into the dropping funnel, wait until the temperature rises to 55°C, start the dropwise addition, and slowly add the solution into the reactor at a rate of 0.1 mL / s, after the dropwise addition, reset the heating temperature to 80°C, stir the reaction for 3 hours, use TLC to confirm that the reaction is complete, and prepare to start purification.

[0040] After the liquid in the reactor was cooled to room temperature, it was taken out in an eggplant-shaped bottle, and the contents of the eggplant-shaped bottle were rotated under reduced pressure at 60°C to remove excess thionyl chloride. After the rotary evaporation was completed, 30 mL of n-hexane was ...

Embodiment 3

[0045] Add 1.66g (10mmol) 3-methoxyphenylacetic acid and magneton into a 50mL three-necked flask, install a condenser tube and a dropping funnel, place the instrument in an oil bath, set the temperature to 55°C, and turn on the stirring and condenser tube , and then add 10mL of thionyl chloride and 0.5mL of N,N-dimethylformamide into the dropping funnel, wait until the temperature rises to 55°C, start the dropwise addition, and slowly add the solution into the reactor at a rate of 0.1 mL / s, after the dropwise addition, reset the heating temperature to 85°C, stir the reaction for 3 hours, use TLC to confirm that the reaction is complete, and prepare to start purification.

[0046] After the liquid in the reactor was cooled to room temperature, it was taken out in an eggplant-shaped bottle, and the contents of the eggplant-shaped bottle were rotated under reduced pressure at 60°C to remove excess thionyl chloride. After the rotary evaporation was completed, 30 mL of n-hexane was ...

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 5-methoxy-2-tetralone, the synthesis method comprises the following steps: reacting 3-methoxyphenylacetic acid with thionyl chloride in the presence of a catalyst solvent to obtain a reaction product containing 3-methoxyphenylacetyl chloride; recrystallizing the obtained product in normal hexane to obtain purified 3-methoxyphenylacetyl chloride; under the condition of a catalyst solvent, reacting the obtained 3-methoxyphenylacetyl chloride with ethylene, and obtaining a reaction product containing 5-methoxy-2-tetralone; and reacting the obtained product with saturated sodium hydrogen sulfite to form salt, and reacting with sodium carbonate for reduction to obtain purified 5-methoxy-2-tetralone. The conditions of the reaction steps are mild, the operation is simple and convenient, the initial raw materials are cheap and easy to obtain, the reaction steps are short, the generated three-waste pollutants are less, the yield is high, the method is suitable for industrial large-scale production, the reaction steps are simplified to a certain extent, and the subsequent reaction is facilitated.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of 5-methoxy-2-tetralone. Background technique [0002] 5-methoxy-2-tetralone is the intermediate for the preparation of medicine rotigotine hydrochloride, and rotigotine hydrochloride is a kind of non-ergot dopamine receptor agonist (DA), which is produced by German Schwartz company ( Schwarz Biosciences) for the adjuvant treatment of early secondary Parkinson's disease and advanced Parkinson's disease. The drug is the first transdermal patch drug for the treatment of Parkinson's disease. The preparation of its intermediate 5-methoxy-2-tetralone plays a decisive role in the whole drug synthesis process. [0003] In the existing synthetic method of rotigotine hydrochloride intermediate 5-methoxy-2-tetralone, 1,6-dihydroxynaphthalene is used as raw material to react with dimethyl sulfate, which is highly toxic substances and the reactio...

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): C07C45/51C07C49/755C07C45/45
CPCC07C45/518C07C45/455C07C303/32C07C51/60C07C2602/28C07C49/755C07C309/25C07C59/64
Inventor 刘生鹏张宇许莉莉吴晓宇熊芸丁一刚樊庆春
Owner WUHAN INSTITUTE OF TECHNOLOGY
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