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Method for preparing 3-methyl-1,3-ferrocenyl propylene-1-one

A technology of bisferrocene-based propylene and acetyl ferrocene is applied in chemical instruments and methods, metallocenes, organic chemistry, etc., and can solve the problems of long reaction time, troublesome post-processing, low yield, etc. The effect of short time, low equipment requirements and easy operation

Active Publication Date: 2013-12-18
SHAANXI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method has a long reaction time, relatively complicated operation, troublesome post-processing, and low yield

Method used

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  • Method for preparing 3-methyl-1,3-ferrocenyl propylene-1-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In the first step, add 2mmol acetyl ferrocene, 1.5mmol NaOH and 3.5mmol K to the mortar 2 CO 3 , grind for 10min, then stand still for 2h to obtain the mixture;

[0024] In the second step, add 50mL of water to the mixture to disperse evenly, then suction filter, wash the filter cake with water until its pH = 7, and dry it at room temperature to obtain a dark red powder that is 3-methyl-1,3- Bisferrocenylpropen-1-one, the yield is 85%; m.p is 120~121℃.

[0025] IR (KBr) (cm -1 ): 3091, 1109, 1006, 819 (C-H of ferrocene ring); 1637 (C=O); 1586 (C=C).

Embodiment 2

[0027] In the first step, add 2mmol acetyl ferrocene, 2mmol KOH and 2.5mmol K to the mortar 2 CO 3 , grind for 15min, then stand still for 1.5h to obtain the mixture;

[0028] In the second step, add 65mL of water to the mixture to disperse evenly, then filter with suction, wash the filter cake with water until its pH=6, and dry it at room temperature to obtain a dark red powder that is 3-methyl-1,3- Bisferrocenyl propen-1-one, the yield is 89%; m.p is 120~121℃.

Embodiment 3

[0030] In the first step, add 2mmol acetyl ferrocene and 3.5mmol NaOH to the mortar, grind for 20min, and then let stand for 2h to obtain the mixture;

[0031] In the second step, add 60mL of water to the mixture to disperse evenly, then filter with suction, wash the filter cake with water until its pH=7, and dry it at room temperature to obtain a dark red powder that is 3-methyl-1,3- Bisferrocenyl propen-1-one, the yield is 92%; m.p is 120~121℃.

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Abstract

The invention provides a method for preparing 3-methyl-1,3-ferrocenyl propylene-1-one. The method comprises the following steps: adding A mmol acetyl ferrocene, B mmol alkali and C mmol K2CO3 into a reaction vessel according to the ratio of A, B and C of 2: (1.5-3.5): (0-3.5), grinding for 10-30 minutes, and then, standing, so as to obtain a mixture; adding water into the mixture to uniformly disperse the mixture, then, carrying out suction filtration, and washing and drying a filter cake, thereby obtaining 3-methyl-1,3-ferrocenyl propylene-1-one. According to the method, a target product is prepared by adopting a grinding method, acetyl ferrocene serves as a raw material, K2CO3 and the alkali serve as a catalyst or the alkali serves as the catalyst alone, the reaction is carried out without solvents, the operation is simple and convenient, the reaction is easy to control, the reaction time is short, the requirements on equipment are low, the after-treatment is simple, and the yield is high.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing 3-methyl-1,3-bisferrocenyl propen-1-one. Background technique [0002] Since the discovery of ferrocene by Kealy and Pauson in 1951, this organometallic compound has attracted people's attention for its unique structure and properties. Due to its aromaticity, thermodynamic stability, photochemical stability, electrophilicity, low toxicity, and redox reversibility, it has been used in various fields, such as: asymmetric catalysis, electrochemical sensors, optical devices, liquid crystal materials, etc. At the same time, ferrocene can pass through the cell membrane and directly interact with intracellular enzymes, DNA or RNA, so it is also widely used in the fields of biology and medicine, such as: anti-tumor, anti-ulcer, anti-spasm, anti-inflammatory , Sterilization, etc. Therefore, the research on ferrocene compounds is very meaningful. [0003] Didier ...

Claims

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Application Information

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IPC IPC(8): C07F17/02
Inventor 刘玉婷殷艳佼尹大伟王捷张韩利吕博
Owner SHAANXI UNIV OF SCI & TECH
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