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Method for preparing ferrocenecarboxaldehyde

A technology of ferrocene formaldehyde and dichloromethane, applied in chemical instruments and methods, metallocenes, organic chemistry, etc., can solve the problems of complex post-processing, low yield, long reaction time, etc., and achieve short reaction time and high yield High efficiency and easy operation

Active Publication Date: 2013-06-12
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method has long reaction time, complex post-processing and low yield

Method used

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  • Method for preparing ferrocenecarboxaldehyde

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0022] In the first step, add 0.07mol DMF (N,N-dimethylformamide) to a dry three-necked flask, add 0.07mol phosphorus oxychloride to it at a rate of 1 drop per second at 8°C, and continue stirring for 0.5 After 2 hours, slowly add 0.01mol of ferrocene, raise the temperature to 20°C at a rate of 1°C / min and react for 2.5h to obtain a mixed solution;

[0023] In the second step, the mixed solution was cooled to room temperature, 21 mL of water was slowly added thereto, the pH of the mixed solution was adjusted to 6 with a 5% NaOH solution, and the mixed solution was extracted twice with dichloromethane, dichloromethane The dosage is 20mL each time, the organic phase obtained after two extractions is combined to obtain the extract phase, the obtained extract phase is washed with water, and then dried with anhydrous magnesium sulfate to remove the moisture in the extract phase, until the anhydrous magnesium sulfate no longer forms block, then decompressed to remove the dichloromet...

Embodiment 2

[0025] In the first step, add 0.08mol DMF to a dry three-necked flask, add 0.08mol phosphorus oxychloride to it at a rate of 2 drops per second at 9°C, continue stirring for 0.5h and then slowly add 0.01mol ferrocene, Raise the temperature to 30°C at a heating rate of 1°C / min and react for 2 hours to obtain a mixed solution;

[0026] In the second step, the mixed solution was cooled to room temperature, 24 mL of water was slowly added thereto, the pH of the mixed solution was adjusted to 7 with a KOH solution with a mass concentration of 10%, and then the mixed solution was extracted twice with dichloromethane, dichloromethane The dosage is 20mL each time, the organic phases obtained after two extractions are combined to obtain the extract phase, the obtained extract phase is washed with water, and then dried with anhydrous sodium sulfate to remove the moisture in the extract phase, until the anhydrous sodium sulfate no longer solidifies block, then decompressed to remove the ...

Embodiment 3

[0028] In the first step, add 0.09mol DMF to a dry three-necked flask, add 0.09mol phosphorus oxychloride to it at a rate of 1 drop per second at 9°C, continue stirring for 0.5h and then slowly add 0.01mol ferrocene, Raise the temperature to 40°C at a heating rate of 2°C / min and react for 1.5h to obtain a mixed solution;

[0029] In the second step, the mixed solution was cooled to room temperature, 27 mL of water was slowly added thereto, the pH of the mixed solution was adjusted to 7 with a 10% NaOH solution, and then the mixed solution was extracted twice with dichloromethane, dichloromethane The dosage is 20mL each time, the organic phase obtained after two extractions is combined to obtain the extract phase, the obtained extract phase is washed with water, and then dried with anhydrous magnesium sulfate to remove the moisture in the extract phase, until the anhydrous magnesium sulfate no longer forms block, then decompressed to remove the dichloromethane in the extract ph...

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Abstract

The invention relates to a method for preparing ferrocenecarboxaldehyde, which comprises the following steps of: adding B mol of DMF (Dimethyl Formamide) into a reaction vessel; adding C mol of phosphorus oxychloride at 8-10 DEG C; adding A mol of ferrocene after continuously stirring for 0.5h; increasing the temperature to 20-60 DEG C and reacting for 1-2.5h to obtain the mixed solution, wherein A:B=1:(7-11); and B=C; cooling the mixed solution to room temperature; adding X mL of water into the mixed solution, wherein X=300B; adjusting the pH of the mixed solution to 6-7 by using NaOH solution or KOH solution; extracting the mixed solution by using methylene dichloride; washing and drying the obtained extracted phase; decompressing and evaporating to remove methylene dichloride in the extracted phase to obtain solid; recrystallizing the obtained solid to obtain ferrocenecarboxaldehyde. According to the invention, a one-pot boiling method is adopted; the method is simple and convenient to operate; the reaction is free from solvents; the reaction can be carried out at 20-60 DEG C; and the method has the advantages of being mild in reaction condition, short in reaction time, simple for post-processing and high in yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing ferrocene formaldehyde. Background technique [0002] The emergence of ferrocene is a milestone in the development of modern chemistry. It has aromaticity, low toxicity and easy substitution, and can prepare various types of derivatives. The research on ferrocene derivatives has become more and more extensive and in-depth, and has been extended to many fields such as medicine, biology, dyes, electrochemistry, liquid crystal materials, and photosensitive materials. Due to the hydrophobicity (lipophilicity) of such derivatives, they can pass through the cell membrane smoothly and act with various enzymes, DNA, RNA and other substances in the cell, so they may be used as drugs for the treatment of certain diseases; Iron derivatives have physiological activities such as antitumor, bactericidal, insecticidal, anemia, anti-inflammation, plant growth regulation,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 尹大伟殷艳佼刘玉婷付青蒋闪闪梁钢涛吕博
Owner SHAANXI UNIV OF SCI & TECH
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