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Diene-butyl ferrocene and preparation method thereof

A dienyl butyl ferrocene and allyl Grignard technology, applied in chemical instruments and methods, metallocenes, organic chemistry, etc., can solve problems such as hindering throughput production and unstable raw materials required for synthesis, and achieve Novel structure, mild reaction conditions, and simple preparation

Inactive Publication Date: 2014-01-22
SUZHOU CINC TEXTILE TECH RP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation of diene propenyl substituted ferrocene has been reported, and the yield reaches 82%, but the instability of the raw materials required for the synthesis may hinder its flux production (see literature: Ogasawara, M.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc., 2002, 124(31), 9068-9069.)

Method used

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  • Diene-butyl ferrocene and preparation method thereof
  • Diene-butyl ferrocene and preparation method thereof
  • Diene-butyl ferrocene and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0035] raw material preparation

[0036] Add 3.100g (16.6mmol) vacuum-dried ferrocene and 12.0mL n-hexane to a dry Schlenk bottle, and stir to form a suspension; then add 25.0mL n-butyl lithium (1.6M, 40.0mmol), and then Add 6.0mL tetramethylethylenediamine (40.0mmol) dropwise within 60min, and continue to stir and react at room temperature for 16h; filter the reaction mixture, and wash the orange-red powder three times with 15.0mL n-hexane to obtain 1 , 1'-dilithium ferrocene is about 15.0mmol, add 35.0mL n-hexane to it, and stir to form a suspension; add 2.8mL (36.0mmol) dimethylformamide to 12mL anhydrous ether, and place in an ice-water bath Add this solution dropwise to the above suspension under cooling (about 30min); remove the ice-water bath after the dropwise addition, let it rise to room temperature naturally and stir for about 30min, add 50.0mL (4.0M, 0.2mol) hydrochloric acid, and continue the reaction for 15min After standing still, the layers were separated, and...

Embodiment 2

[0048] raw material preparation

[0049] Add 3.071g (16.5mmol) vacuum-dried ferrocene and 12.0mL n-hexane to a dry Schlenk bottle, stir to form a suspension; then add 25.0mL n-butyl lithium (1.6M, 40.0mmol), and then Add 6.0 mL of tetramethylethylenediamine (40.0 mmol) dropwise within 60 minutes, and continue to stir and react at room temperature for 16 hours; filter the reaction mixture, and wash the obtained orange-red powder three times with 15.0 mL of n-hexane to obtain 1, 1'-Lithium ferrocene is about 15.0mmol, add 35.0mL n-hexane to it, stir to form a suspension; add 2.8mL (36.0mmol) dimethylformamide to 12mL anhydrous ether, cool in an ice-water bath Add this solution dropwise to the above suspension (about 30min); after the dropwise addition, remove the ice-water bath, naturally warm up to room temperature and stir for about 30min, add 50.0mL (4.0M, 0.2mol) hydrochloric acid to continue the reaction for 15min, and then separate The aqueous layer was extracted three ti...

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Abstract

The invention relates to diene-butyl ferrocene and a preparation method thereof. The preparation method comprises the steps of taking ferrocene dialdehyde as a raw material, and dropping an allyl Grignard reagent in an ice-water bath to obtain 1, 1'-bis (1-hydroxy-3-butenyl) ferrocene; further performing reflux on the compound in an acetic acid / methanol solution, and reacting to obtain 1, 1'-bis (1-methoxy-3-butenyl). The diene-butyl symmetrical substituted ferrocene is an important synthesis intermediate, and double bonds further endow the compound with the capability of participating in polymerization reaction, so that the diene-butyl ferrocene is a novel ferrocene-based monomer.

Description

technical field [0001] The present invention relates to a dienyl butyl ferrocene and a preparation method thereof, in particular to a ferrocene dialdehyde as the main raw material, which is hydrolyzed to obtain 1,1'-bis(1 -Hydroxy-3-butenyl)ferrocene; further etherification of hydroxymethyl gives 1,1'-bis(1-methoxy-3-butenyl)ferrocene; symmetrical double bond endows it with participation The ability of the polymerization reaction and the new material for synthesizing other ferrocene derivatives belong to the technical field of functional materials. Background technique [0002] Ferrocene derivatives have unique optical, electrical, and magnetic properties, and have attracted much attention because of their wide range of industrial applications. Especially ferrocene derivatives containing unsaturated double bonds, on the one hand, due to the existence of ferrocene in the structure, have obvious absorption characteristics of ultraviolet-visible light; reaction, they can be u...

Claims

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Application Information

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IPC IPC(8): C07F17/02C08F30/04
Inventor 王建军翟涛牛梓潞朱慧霞程丝
Owner SUZHOU CINC TEXTILE TECH RP
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