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Method for synthesizing acyl ferrocene

A technology of acetyl ferrocene and sodium acetate, applied in chemical instruments and methods, metallocene, organic chemistry and other directions, can solve problems such as low yield, and achieve the effects of increased yield and less dosage

Inactive Publication Date: 2008-12-17
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of acyl ferrocene basically all adopts above-mentioned method at present stage, and all there is common defect in above-mentioned method: the one, productive rate is not high, the 2nd, there are two substitution products, the 3rd, need to separate with column chromatography just can reach certain. purity

Method used

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Examples

Experimental program
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Effect test

example 1

[0008] [Example 1]: Add 3.72Kg (20mol) ferrocene and 2.1L (21mol) acetic anhydride to a clean and dry reactor, dissolve with 15L dichloromethane, cool to 0°C, and slowly add 6L tris The mixed solution of boron fluoride diethyl ether and 10L of dichloromethane was stirred for 1 hour, and stirred for 4 hours at room temperature until the reaction was complete. The reaction mixture was added in batches to an excess of saturated sodium acetate aqueous solution at 0° C., and the layers were separated after standing. The organic phase was separated, and the aqueous phase was extracted twice with 15 L of dichloromethane. The organic phases were combined, washed successively with 10L deionized water, 10L saturated sodium bicarbonate solution until alkaline, and deionized water until neutral, added anhydrous magnesium sulfate, dried for 4 hours, and filtered. Add 30L of 90-120°C petroleum ether to the filtrate, concentrate to 30L, cool and crystallize, filter, and wash the filter cake ...

example 2

[0009] [Example 2]: Add 7.44Kg (40mol) ferrocene and 4.1L (41mol) acetic anhydride to a clean and dry reactor, dissolve with 25L dichloromethane, cool to 4°C, slowly add 12L tri The mixed solution of boron fluoride diethyl ether and 20L of dichloromethane was stirred for 1 hour, and stirred at room temperature for 2 hours. The reaction mixture was added in batches to an excess of saturated sodium acetate aqueous solution at 4°C, and the layers were separated after standing. The organic phase was separated, and the aqueous phase was extracted twice with 30 L of dichloromethane. The organic phases were combined, washed successively with 20L deionized water, 20L saturated sodium bicarbonate solution until alkaline, and deionized water until neutral, added anhydrous magnesium sulfate, dried for 4 hours, and filtered. Add 60L of 90-120°C petroleum ether to the filtrate, concentrate to 60L, cool and crystallize, filter, and wash the filter cake with a small amount of petroleum ether...

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Abstract

The invention discloses a method for synthesizing acetyl ferrocene. The main method is to use acetic anhydride as an acylating agent and boron trifluoride diethyl ether as a catalyst to react at room temperature for 3 to 4 hours. The method overcomes the defects of low yield, disubstituted products, and the need for column chromatography to achieve higher purity in the existing synthetic method of acetylferrocene, so that the yield is significantly improved, and there is no disubstituted product; acid anhydride The dosage is small, only 5% excess is required; high-purity products can be obtained without column chromatography separation.

Description

technical field [0001] The invention relates to a method for synthesizing acetyl ferrocene, in particular to a method for synthesizing acetyl ferrocene by using ferrocene and acetic anhydride. Background technique [0002] The ferrocene group has aromaticity, redox property and low toxicity, and its derivatives have a wide range of applications in the fields of polymers, electrochemistry, and medicine. Introducing ferrocene groups into different molecules in order to obtain new compounds or compounds with special properties is a hot spot in the research of ferrocene chemistry in recent years. Since the acyl group contained in the acyl ferrocene is a chemically active group, it is an important intermediate for the synthesis of ferrocene derivatives. [0003] The synthesis of acyl ferrocene mostly adopts Friedel-Crafts acylation reaction. The commonly used acylating reagents are acid anhydride, acid chloride, carboxylic acid, etc., and the catalyst used is Lewis acid, such as...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02
Inventor 刘明国廖全斌
Owner CHINA THREE GORGES UNIV