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Method for high-selectivity synthesis of 9-fluorenylcarbinol

A high-selectivity, methanol technology, applied in chemical instruments and methods, preparation of organic compounds, separation/purification of hydroxyl compounds, etc., can solve problems such as difficulty in operation process, low selectivity, complex process, etc., to reduce impact, The effect of improving reduction efficiency and simplifying operation steps

Pending Publication Date: 2021-06-04
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the reaction needs to be carried out at two different temperatures, the operation process has certain difficulties
[0009] In the second step reduction reaction, when formaldehyde is used as reducing agent, there are more by-products, its selectivity is low and the reaction conditions are not easy to control; while metal borohydride is used as reducing agent with high selectivity and few by-products, but due to boron Sodium hydride is easily hydrolyzed in water, and 9-fluorenaldehyde needs to be separated from the acylation reaction system quenched by water, and then dissolved in methanol, ethanol and other solvents for reduction, so a solvent conversion process must be involved, which increases the operation complexity of
[0010] Therefore, the currently reported two-step method for synthesizing 9-fluorenylmethanol has a long period and complicated process.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 1.66g fluorene and 20mL DMSO to a jacketed reactor equipped with a magnetic stirrer and a condenser, and heat to 55°C at a stirring rate of 300r / min. After the solid dissolves, add 7mL of 20% sodium ethoxide-ethanol solution , slowly added 1.2 mL of ethyl formate, reacted under nitrogen protection for 70 min, added 20 mL of water to quench the reaction, and prepared 9-fluorenaldehyde.

[0029] Remove the condenser tube and nitrogen, add 1.65g CaCl to the DMSO solution of 9-fluorenaldehyde obtained 2 , stirred to form a uniform suspension, and then added 0.46 g of sodium borohydride. After reacting at room temperature for 90 minutes, the reaction liquid was taken and detected by GC, and the content of 9-fluorenemethanol was nearly 100%.

[0030] The pH value of the reaction solution was adjusted to 7.0-7.5 with 2mol / L HCl solution, and a white solid precipitate of 9-fluorenemethanol was precipitated. After filtering off the solid 9-fluorenylmethanol, it was dried t...

Embodiment 2

[0035] Add 1.66g fluorene and 20mL DMSO to a jacketed reactor equipped with a magnetic stirrer and a condenser, and heat to 50°C at a stirring rate of 300r / min. After the solid dissolves, add 8mL of 20% sodium ethoxide-ethanol solution , slowly added 2 mL of ethyl formate, reacted under nitrogen protection for 65 min, added 20 mL of water to quench the reaction, and prepared 9-fluorenaldehyde.

[0036] Remove the condenser tube and nitrogen, add 2.22g CaCl to the DMSO solution of 9-fluorenaldehyde obtained 2 , stirred to form a uniform suspension, and then added 0.57 g of sodium borohydride. After reacting at room temperature for 90 minutes, the reaction liquid was taken and detected by GC, and the content of 9-fluorenemethanol was nearly 100%.

[0037] The pH value of the reaction solution was adjusted to 7.0-7.5 with 1mol / L HCl solution, and a white solid precipitate of 9-fluorenemethanol was precipitated. After filtering off the solid 9-fluorenylmethanol, it was dried to ...

Embodiment 3

[0042] Add 1.66g fluorene and 25mL DMSO to a jacketed reactor equipped with a magnetic stirrer and a condenser, and heat to 50°C at a stirring rate of 300r / min. After the solid dissolves, add 8mL of 20% sodium ethoxide-ethanol solution , slowly add 2 mL of ethyl formate, react under nitrogen protection for 65 min, add 25 mL of water to quench the reaction, and prepare 9-fluorenaldehyde.

[0043] Remove condenser tube and nitrogen, add 2.46g Ca(NO 3 ) 2 , stirred to form a uniform suspension, and then added 0.38 g of sodium borohydride. After 120 minutes of reaction at room temperature, the reaction liquid was taken and detected by GC, and the content of 9-fluorenemethanol was nearly 100%.

[0044] The pH value of the reaction solution was adjusted to 7.0-7.5 with 2mol / L HCl solution, and a white solid precipitate of 9-fluorenemethanol was precipitated. After filtering off the solid 9-fluorenylmethanol, it was dried to obtain 9-fluorenylmethanol.

[0045] Add ice cubes to t...

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Abstract

The invention discloses a method for high-selectivity synthesis of 9-fluorenylcarbinol. The method comprises the following steps: heating and dissolving fluorene in a DMSO solvent system at 50-55 DEG C in the presence of a sodium ethoxide ethanol solution alkali catalyst, adding an acylation reagent ethyl formate, carrying out acylation reaction at the same temperature to prepare 9-fluorenylformaldehyde, adding a soluble metal inorganic salt auxiliary agent, then using NaBH4 for a reduction reaction, adjusting the pH value of reaction liquid to be neutral, and separating out 9-fluorene methanol solid sediment. According to the method disclosed by the invention, fluorene is completely converted by utilizing a section of temperature, the 9-fluorene methanol can be obtained through high-selectivity reduction without solvent conversion by adding the soluble metal inorganic salt auxiliary agent, and the yield of the 9-fluorene methanol is improved on the premise of shortening the reaction time.

Description

technical field [0001] The invention relates to a method for preparing 9-fluorenemethanol, in particular to a method for preparing 9-fluorenemethanol by using fluorene as a raw material. Background technique [0002] 9-fluorenemethanol is the raw material for the preparation of polypeptide Fmoc protecting agent, used as carboxyl protecting agent, internal electron donor of Ziegler-Natta catalyst, etc. At the same time, as a very important chemical intermediate, 9-fluorenemethanol is widely used in the fields of biomedicine, functional pigments and polymers, and its demand is constantly increasing. Fluorene is the main component of coal tar, and its content in coal tar is 1 to 2%. my country has abundant fluorene resources, and it is of great significance to use cheap fluorene as raw material to produce high value-added 9-fluorenemethanol. [0003] At present, the methods for synthesizing 9-fluorenemethanol from fluorene mainly include one-step synthesis method and two-step...

Claims

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Application Information

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IPC IPC(8): C07C33/34C07C29/14
CPCC07C29/14C07C29/76C07C45/455C07C2603/18C07C33/34C07C47/453Y02P20/52
Inventor 叶翠平郭美鑫李文英梁美生
Owner TAIYUAN UNIV OF TECH
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