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Method for synthesizing dicyclohexyl o-fluoroethylbenzene liquid crystal compound

A liquid crystal compound, bicyclohexyl technology, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problem of high cost, achieve the effect of improving yield and purity, improving purity, and enhancing the feasibility of industrial production

Inactive Publication Date: 2013-04-10
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] First prepare the trans-alkyl bicyclohexyl m-fluorobenzene, and then obtain the target product through Fuckers acylation and Huang Minglong reduction. This synthetic method uses the precious raw material alkane (oxygen) base bicyclohexyl ketone as the reaction starting material, so the cost is relatively low. high

Method used

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  • Method for synthesizing dicyclohexyl o-fluoroethylbenzene liquid crystal compound
  • Method for synthesizing dicyclohexyl o-fluoroethylbenzene liquid crystal compound
  • Method for synthesizing dicyclohexyl o-fluoroethylbenzene liquid crystal compound

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Add 43ml of 11.2mol / L concentrated hydrochloric acid and 120ml of water to a 1L three-necked flask, slowly add 95g of o-fluoro-p-bromoaniline dropwise under heating and stirring, heat until dissolved, cool, add 45ml of hydrochloric acid under stirring, keep in an ice-water bath for 1.5 hours, use dropwise Add a funnel below the liquid surface and slowly add 60ml of aqueous solution containing 35g of sodium nitrite, and continue stirring for 1 hour after the dripping is complete. Sodium acetate aqueous solution adjusts the pH value of the reaction system to be approximately equal to 5, quickly filters out a small amount of deep red solid in the solution, and puts the light yellow diazonium salt solution in the refrigerator for use.

Embodiment 2

[0022] Add 200ml of water, 15g of copper sulfate pentahydrate, and 42g of acetic acid to the there-necked flask, stir and dissolve, then add 28.2g of 10% aqueous solution of acetaldehyde oxime, 1.Sg of sodium sulfite and stir for 10 minutes, then adjust the pH value of the system to neutral with sodium acetate , lower the temperature to below 10°C, slowly add the diazonium salt solution below the liquid level with a dropping funnel under rapid stirring, continue stirring for 1 hour, add 240ml of toluene, stand to separate the organic layer, and obtain compound (II).

Embodiment 3

[0024] Add the organic phase obtained in the above example into a three-necked flask, add 240ml of water and 300ml of 11.2mol / L concentrated hydrochloric acid, heat to reflux for 3 hours, cool to room temperature, separate the organic phase, and wash the organic phase with 200ml of 5% aqueous sodium carbonate To neutrality, the aqueous phase was extracted with 100ml of ether, then dried with 50g of anhydrous magnesium sulfate, and rectified under reduced pressure to obtain compound (III).

[0025] The yield is 73%; the gas phase purity is 98%.

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Abstract

The invention provides a method for synthesizing a dicyclohexyl o-fluoroethylbenzene liquid crystal compound, comprising the following steps: (1) using o-fluoro-p-bromoaniline as the raw material to react with sodium nitrite in the presence of hydrochloric acid to generate a compound (I); (2) reacting the compound (I) with acetaldoxime under the catalysis of blue copperas to obtain a compound (II); (3) hydrolyzing the compound (II) with hydrochloric acid to obtain a compound (III); (4) carrying out Huang-Minlon reduction on the compound (III) to obtain a compound (IV); (5) preparing the compound (IV) into a grignard reagent in tetrahydrofuran or diethyl ether, then reacting the grignard reagent with alkyldicyclohexylanone, and acidizing and dehydrating the reactant to obtain a compound (V); and (6) carrying out hydrogenation reduction on the compound (V) to obtain the compound shown in the molecular formula. By synthesizing the intermediate o-fluoro-p-bromoethylbenzene, the invention provides a new method for synthesizing bicyclohexane liquid crystal compound. The method is simple to operate and safe and can effectively improve the purity and the yield of the target compound.

Description

technical field [0001] The invention relates to a synthesis method of a class of bicyclohexyl-o-fluoroethylbenzene liquid crystal compounds, in particular to a synthesis method of a class of bicyclohexyl o-fluoroethylbenzene liquid crystal compounds. Background technique [0002] Since the 1970s, with the development of liquid crystal optics, liquid crystal chemistry, and large-scale integrated circuits and liquid crystal materials, the application of liquid crystals in display has achieved rapid development, and has successively experienced TN-LCD, STN-LCD , TFT-LCD three stages. Its typical applications include watches, calculators, instruments and meters, and later MP3 and MP4, which are now widely used in LCD TVs. Liquid crystal display has the advantages of flat plate, light weight, low energy consumption, low radiation, etc., and the processing technology is continuously improved, the cost is continuously reduced, and its popularity rate is rapidly increasing. As LCD...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/18C07C17/354C07C43/192C07C41/20
Inventor 姜天孟田会强杭德余陈海光储士红高立龙程献龙
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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