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2,3,5-Trifluoro-4-difluoro(3,4,5-trifluorophenylol)methyl-benzaldehyde, its synthetic method and its application in preparation of liquid crystal compound

A technology of trifluorophenol and compounds, which is applied in the application field of preparing liquid crystal compounds, can solve the problems of unsuitability for industrial production, high raw material prices, difficult purification of products, etc., and achieve easy industrial production, low purchase cost and good yield Effect

Active Publication Date: 2015-04-15
JIANGSU HECHENG ADVANCED MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports on the preparation method of this type of compound, and the price of its raw materials is high, and the product in the preparation process is difficult to purify, which makes the cost higher and is not suitable for industrial production.

Method used

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  • 2,3,5-Trifluoro-4-difluoro(3,4,5-trifluorophenylol)methyl-benzaldehyde, its synthetic method and its application in preparation of liquid crystal compound
  • 2,3,5-Trifluoro-4-difluoro(3,4,5-trifluorophenylol)methyl-benzaldehyde, its synthetic method and its application in preparation of liquid crystal compound
  • 2,3,5-Trifluoro-4-difluoro(3,4,5-trifluorophenylol)methyl-benzaldehyde, its synthetic method and its application in preparation of liquid crystal compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060]

[0061] 1) Synthesis of Compound 2

[0062] Weigh 120g of zinc powder and add it into a 2L three-necked bottle, then add 60g of compound 1, add 1200mL of ammonia water into the bottle, and mechanically stir for 40h.

[0063] The reaction solution was poured into ice water, adjusted to pH=1-2 with concentrated hydrochloric acid, extracted with dichloromethane and recrystallized with ethyl acetate+petroleum ether to obtain 42.8g of white solid. Reaction with boron trifluoride ether and ethanol proved to be compound 2 with a purity of 95%. MS m / z: 204 (M + ), yield: 78.7%. For the MS diagram of compound 2, see figure 1 .

[0064] 2) Synthesis of Compound 3

[0065] Weigh 49g of zinc chloride and add it to a 1L single-necked bottle, add 500mL of tetrahydrofuran, add 27.4g of sodium borohydride in batches, stir at room temperature for 2 hours, slowly add 42.8g of compound 2 dropwise, slowly raise the temperature to 72°C, and react after 3 hours completely.

[0066...

Embodiment 2

[0094]

[0095] Weigh 27.5g of compound 8 synthesized in Example 1, 12g of ethyl propylene glycol, and 1.3g of p-toluenesulfonic acid into a 500mL single-necked bottle, add 200mL of toluene, and reflux at 135°C for 5h. TLC monitors that the reaction is complete.

[0096] After the reaction of the raw materials was completed, it was quenched with water, and the organic layer was separated, extracted twice with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous sodium sulfate, and filtered. The organic phase was spin-dried, and petroleum ether was roughly passed through the column, and then distilled under reduced pressure to obtain 12 g of white crystal compound 11, GC: 99%, yield: 35.2%.

[0097] Liquid crystal properties of compound 11:

[0098] Δn: 0.0795;

[0099] Δε: 19.4;

[0100] Cp: ​​-29.2.

Embodiment 3

[0102]

[0103] Weigh 27.5g of compound 8 synthesized in Example 1, 14g of 2-ethoxy-1,3-propanediol, and 1.3g of p-toluenesulfonic acid, add them to a 500mL single-necked bottle, add 200mL of toluene, and reflux at 135°C for 5h , TLC monitors that the reaction is complete.

[0104] After the reaction of the raw materials was completed, the mixture was quenched with water, and the organic layer was separated, extracted twice with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous sodium sulfate, and filtered. The organic phase was spin-dried, and petroleum ether was roughly passed through the column, and then distilled under reduced pressure to obtain 14 g of white crystal compound 12, GC: 99.2%, yield: 39.5%.

[0105] Liquid crystal properties of compound 12:

[0106] Δn: 0.0812;

[0107] Δε: 22.2;

[0108] Cp: ​​-15.4.

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Abstract

The invention provides 2,3,5-trifluoro-4-difluoro(3,4,5-trifluorophenylol)methyl-benzaldehyde (a compound of formula 8), and its preparation method. The compound can be used to synthesize a compound with the structure represented by formula I as an intermediate compound. The compound of formula 8 is prepared from 2,3,4,5-tetrafluorobenzoic aid. The method has the advantages of simple operation, high yield, low cost, and suitableness for industrial production.

Description

technical field [0001] The invention relates to the field of liquid crystals, in particular to a new intermediate 2,3,5-trifluoro-4-difluoro(3,4,5-trifluorophenol)methyl-benzaldehyde for preparing liquid crystal compounds, and Its preparation method and its application in the preparation of liquid crystal compounds. Background technique [0002] Since the discovery of liquid crystals in 1988, liquid crystals have broad application prospects due to their many unique properties. For example, in the chemical industry, liquid crystals can be used as ordered solvents to promote organic chemical orientation reactions, stereoisomer selection, enrichment and separation of optically active substances, and as chromatographic stationary liquids to improve chromatographic selectivity and separation efficiency; liquid crystal state functional separation membranes It has the best separation efficiency with selective permeability. In the electronics industry, liquid crystals are widely u...

Claims

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Application Information

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IPC IPC(8): C07C47/575C07C45/30C07D319/06C07C63/70C07C51/377C09K19/34
Inventor 刘琦徐爽朱煜剑谭玉东靳灿辉孙仲猛曹林法
Owner JIANGSU HECHENG ADVANCED MATERIALS
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