Synthesis method of 4-(3-butene-1-yl)-4'-alkyl-1, 1'-biphenyl liquid crystal monomer

A technology of liquid crystal monomers and synthesis methods, which is applied in the direction of liquid crystal materials, chemical instruments and methods, hydrocarbons, etc., and can solve problems such as unfavorable resource conservation and environmental protection, unfavorable industrial production requirements, and a total yield of less than 60%. , to achieve the effects of large-scale production, low cost and short synthetic route

Pending Publication Date: 2021-06-29
烟台盛华液晶材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This method uses two kinds of liquid crystal intermediates to carry out Suzuki coupling using expensive palladium catalysts, among which aryl boronic acid is a conventional commercially available product, and another brominated aromatic hydrocarbon intermediate needs at least three steps to be prepared, and the market can only be purchased by customization; The coupled biphenyl intermediates are then synthesized in three steps of deprotection and Witting reaction. The reaction steps are long, the total yield is less than 60%, and the cost is high; triphenylphosphine oxide waste is produced, which is atom-economical. Low, serious environmental pollution, not conducive to resource conservation and environmental protection, not conducive to sustainable development of industrial production requirements

Method used

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  • Synthesis method of 4-(3-butene-1-yl)-4'-alkyl-1, 1'-biphenyl liquid crystal monomer
  • Synthesis method of 4-(3-butene-1-yl)-4'-alkyl-1, 1'-biphenyl liquid crystal monomer
  • Synthesis method of 4-(3-butene-1-yl)-4'-alkyl-1, 1'-biphenyl liquid crystal monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1, the synthetic method of 4-(3-butene-1-methyl)-4'-methyl-1,1'-biphenyl, is as follows:

[0029]1) Under the protection of nitrogen, add 3 grains of iodine, 3.51g of magnesium chips, 6.2g of lithium chloride and 50ml of tetrahydrofuran into a 1L dry and clean three-necked flask, install a stirring device, constant pressure dropping funnel, drying device, nitrogen protection, thermometer and Heating device, dropwise add 30g of 4-bromo-4′-methyl-1,1′-biphenyl in 200ml tetrahydrofuran solution, raise the temperature to 50°C and trigger, then add the remaining 4-bromo-4′ dropwise at 25°C to 50°C -Methyl-1,1'-biphenyl solution, after the dropwise addition, the reflux reaction time is 20 to 35 minutes, and the sample is tested by GC. The content of 4-bromo-4'-methyl-1,1'-biphenyl is required to be ≤0.0050%, and the preparation Good Grignard reagent is kept at 25°C for use;

[0030] 2) Under nitrogen protection, add 1.57g Co(acac)2 and 100mL tetrahydrofuran to a 2L d...

Embodiment 2

[0031] Example 2, the synthesis method of 4-(3-butene-1-methyl)-4'-methyl-1,1'-biphenyl, is as follows:

[0032] 1) Under nitrogen protection, add 3 grains of iodine, 3.51g magnesium chips, 5.74g lithium chloride and 50ml tetrahydrofuran into a 1L dry and clean three-necked flask, install a stirring device, constant pressure dropping funnel, drying device, nitrogen protection, thermometer and Heating device, dropwise add 30g of 4-bromo-4′-methyl-1,1′-biphenyl in 200ml tetrahydrofuran solution, raise the temperature to 50°C and trigger, then add the remaining 4-bromo-4′ dropwise at 25°C to 50°C -Methyl-1,1'-biphenyl solution, after the dropwise addition, the reflux reaction time is 20 to 35 minutes, and the sample is tested by GC. The content of 4-bromo-4'-methyl-1,1'-biphenyl is required to be ≤0.0050%, and the preparation It is better to keep the Grignard reagent at 25°C for use.

[0033] 2) Under nitrogen protection, add 5.58g Co(PPh)2Cl2, 100mL dioxane and 24.15g N-methylp...

Embodiment 3

[0034] Example 3, the synthesis method of 4-(3-butene-1-methyl)-4'-methyl-1,1'-biphenyl, is as follows:

[0035] 1) Under nitrogen protection, add 3 grains of iodine, 3.51g magnesium chips, 6.98g lithium chloride and 50ml tetrahydrofuran into a 1L dry and clean three-necked flask, install a stirring device, constant pressure dropping funnel, drying device, nitrogen protection, thermometer and Heating device, dropwise add 30g of 4-bromo-4′-methyl-1,1′-biphenyl in 200ml tetrahydrofuran solution, raise the temperature to 50°C and trigger, then add the remaining 4-bromo-4′ dropwise at 25°C to 50°C -Methyl-1,1'-biphenyl solution, after the dropwise addition, the reflux reaction time is 20 to 35 minutes, and the sample is tested by GC. The content of 4-bromo-4'-methyl-1,1'-biphenyl is required to be ≤0.0050%, and the preparation It is better to keep the Grignard reagent at 25°C for use.

[0036] 2) Under nitrogen protection, add 0.79g CoCl2 and 2.62g MnBr2 and 100mL ethylene glycol...

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PUM

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Abstract

The invention discloses a synthesis method of a 4-(3-butene-1-yl)-4'-alkyl-1, 1'-biphenyl liquid crystal monomer. The synthetic route is shown in the description, wherein R is a straight chain alkyl group with 1-3 carbon atoms. The synthesis method has the characteristics that cheap and easily available raw materials are adopted, the reaction steps are short, the use of organic phosphine salt is avoided, the operation is simple, the atom economy is high, and no organic phosphine pollutant is discharged.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal monomer compounds, and in particular relates to a synthesis method of a 4-(3-buten-1-yl)-4'-alkyl-1,1'-biphenyl liquid crystal monomer. Background technique [0002] Organic magnesium reagents such as RMgX (X is a halogen, R is a hydrocarbon group) and RMgR, commonly known as Grignard Reagent, were discovered by French chemist Francois Agust Victor Grignard in 1900. With the characteristics of economical and easy-to-obtain synthetic raw materials, direct and simple synthetic methods, and high reactivity, Grignard reagents have become organometallic reagents commonly used in organic synthesis. At the same time, the Kumada reaction discovered in the 1970s set off Grignard reagents in transition gold catalysis. The C-C Coupling Reaction Applied Boom. [0003] In the prior art, biphenyl liquid crystal monomers are generally prepared by Suzuki coupling with expensive palladium catalysts, result...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/32C07C15/50C09K19/12
CPCC07C1/326C09K19/12C09K2019/122C07C15/50
Inventor 阮群奇石志亮李坤李志广李明政宋燕张慧勤梁斌纪显光高跟华范俊艳王玉洁
Owner 烟台盛华液晶材料有限公司
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