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

Simple preparation process of 9-fluorenemethanol

A technology for methanol preparation and methanol, which is applied in the field of preparation of 9-fluorenemethanol, can solve problems such as unfavorable scale-up production, large product loss, and incomplete reaction, and achieve the goals of avoiding production safety hazards, improving the purity of recrystallization, and improving the purity Effect

Inactive Publication Date: 2013-10-16
ZHANG JIA GANG VINSCE BIO PHARM
View PDF5 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The second step is to reduce 9-fluorenaldehyde to 9-fluorenemethanol, and reduce it with formaldehyde aqueous solution, the reaction is not complete, and the yield is low
[0007] 1. The catalyst sodium hydride produces a large amount of hydrogen during the heating reaction process, which poses a great safety hazard
[0008] 2. Formaldehyde aqueous solution is used as a reducing agent. Since 9-fluorenemethanol is insoluble in water, the reaction produces solids, which makes the reaction incomplete, and the yield is low, which is not conducive to large-scale production
[0009] 3. The crude product 9-fluorenemethanol is generally purified by solvent recrystallization, and the solvents used include toluene, ethanol, ether, etc., resulting in a great loss of the product

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

Embodiment 1

[0022] Preparation of 9-Fluorenaldehyde

[0023] Take 15g of sodium ethoxide and 100ml of tetrahydrofuran into a four-necked bottle, turn on the magnetic stirring, and after 30 minutes, dissolve 50g of industrial fluorene into 300-350ml of tetrahydrofuran and add it dropwise to the reaction bottle. After half an hour of dripping, react for 2-3 hours and add 100ml ethyl formate, molar equivalent 4-5, heat up to 30-40°C, react for about 12 hours, pour into ice water, wash with 100ml of petroleum ether in two equal parts, use acetic acid to make the water phase acidic, and use 200ml di Chloromethane was washed and extracted twice, and the organic phase was washed twice with saturated saline, left to stand and separated, dried with anhydrous sodium sulfate, filtered, concentrated and recovered to dichloromethane to obtain 9-fluorenaldehyde, no impurities on the TLC plate .

Embodiment 2

[0025] Preparation of 9-Fluorenaldehyde

[0026] Take 15g of sodium ethoxide and 50ml of dimethylformamide into a four-neck bottle, turn on the magnetic stirring, and after 30 minutes, dissolve 50g of industrial fluorene into 200-250ml of dimethylformamide and drop them into the reaction bottle, and drop them in half an hour After reacting for 2-3 hours, add 100ml of ethyl formate, raise the temperature to about 60°C, react for about 12 hours, pour into ice water, wash with 100ml of petroleum ether in two equal parts, use acetic acid to make the water phase acidic, and use 200ml of bismuth Chloromethane was washed and extracted twice, and the organic phase was washed twice with saturated saline, left to stand and separated, dried with anhydrous sodium sulfate, filtered, concentrated and recovered to dichloromethane to obtain 9-fluorenaldehyde, no impurities on the TLC plate .

Embodiment 3

[0028] Preparation of 9-fluorenemethanol

[0029] Under ice bath, mix the 9-fluorenaldehyde obtained in the previous step, 100-120ml methanol, about 5g NaBH 4 , added to a three-neck flask, stirred at room temperature for about 3 hours, then poured the reaction solution into water and stirred, and a large amount of white solid was formed. After filtration, the filter cake was vacuum-dried at 60°C for 2 hours to obtain about 49 g of The crude product of 9-fluorenylmethanol, the purity of 9-fluorenylmethanol in the crude product is about 92%, and the yield is about 84%.

[0030] Dissolve the crude product of 9-fluorenemethanol with a purity of about 92% according to the mass ratio of crude product:petroleum ether=1:12, then perform hot filtration, and slowly cool the filtrate to about 0°C, a large number of white needle-like crystals precipitate out , filtered, and vacuum-dried the filter cake at 60°C for 2 hours to obtain 9-fluorenemethanol with a purity greater than 99%; the ...

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 method for preparation of 9-fluorenemethanol, especially to an improved preparation method of 9-fluorenemethanol. The method comprises the steps of: 1) preparing industrial fluorene, sodium ethoxide, ethyl formate and tetrahydrofuran in a ratio of 50g:15g:50ml:200ml, adding tetrahydrofuran of sodium ethoxide into a four-mouth bottle, controlling the temperature at 0-10DEG C, adding a tetrahydrofuran solution of industrial fluorene dropwisely, adding ethyl formate, and raising the temperature to 30-40DEG C, thus obtaining 9- fluorenecarboxaldehyde; and 2) adding methanol and NaBH4 under ice bath, conducting reduction to obtain a 9-fluorenemethanol crude product, carrying out recrystallization so as to obtain white needlelike 9-fluorenemethanol. The crude product purity is enhanced, the reaction conditions are mild, and the cost is lowered, so that the method is easy for industrialization.

Description

technical field [0001] The invention relates to a method for preparing 9-fluorenemethanol, in particular to an improved method for preparing 9-fluorenemethanol from fluorene. Background technique [0002] As an amino-protecting reagent, fluorenylmethoxycarbonyl chloride is widely used in the field of peptide synthesis. Its stability under acidic conditions and easy detachment under alkaline conditions play a great role in promoting the development of the biological field and the research and development of new drugs. Auxiliary role, 9-fluorenemethanol is used as a raw material for the preparation of fluorenylmethoxycarbonyl chloride intermediates. It is also an important drug itself, and has a good therapeutic effect on drug-resistant falciparum malaria and rodent malaria. It is used as a phosphoric acid in the synthesis of deoxyribonucleotides. The demand for ester protecting groups and carboxyl protecting groups is increasing; my country's industrial fluorene is rich in reso...

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): C07C33/34C07C29/14
Inventor 彭学东张梅赵金召庞珍强
Owner ZHANG JIA GANG VINSCE BIO PHARM
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