2,2'-bialkoxyl-4,4'-biphenyl dicarboxylic acid and synthesis method thereof

A synthesis method and compound technology, applied in 2 fields, can solve the problems of low yield and the like, and achieve the effects of high yield, improved practicability, and simple operation

Inactive Publication Date: 2012-03-21
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] One of the purposes of the present invention is to provide a new substance 2,2'-dialkoxy-4,4'-biphenyl dicarboxylic acid, another purpose of the present invention is to provide 2,2'-dialkoxy -the synthetic method of 4,4'-biphenyl dicarboxylic acid; the third purpose of the present invention is to overcome the low yield of prior art and improve 2,2'-dihydroxy-4,4'-biphenyl dicarboxylic acid synthesis method

Method used

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  • 2,2'-bialkoxyl-4,4'-biphenyl dicarboxylic acid and synthesis method thereof
  • 2,2'-bialkoxyl-4,4'-biphenyl dicarboxylic acid and synthesis method thereof
  • 2,2'-bialkoxyl-4,4'-biphenyl dicarboxylic acid and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of 2,2'-dimethoxy-4,4'-biphenyldicarboxylic acid

[0033] A, the preparation of 4-iodo-3-hydroxybenzoic acid

[0034] Iodine (7.82g, 30.7mmol) and KI (6.10g, 36.5mmol) were dissolved in 34mL of water, and it was added dropwise to the mass of 3-hydroxybenzoic acid (4.60g, 33.3mmol) within 15 minutes under stirring. The concentration is 26% ammonia water (67mL) solution, and continue to stir for 25 minutes. Acidify with 37% hydrochloric acid by mass percent, and separate the precipitate by suction filtration. The filtrate was extracted with ethyl acetate (60×3mL), and the solid separated from the extract was combined with the precipitate obtained by suction filtration, washed with water, and recrystallized to obtain white crystals of 4-iodo-3-hydroxybenzoic acid (4.30g, 16.4mmol). rate of 62%.

[0035] 1 H NMR (d 6 -DMSO): δ 7.13-7.14 (d, 1H), 7.42 (s, 1H), 7.79-7.81 (d, 1H).

[0036] B, the preparation of 4-iodo-3-methoxybenzoic acid methyl e...

Embodiment 2

[0045] Example 2: Preparation of 2,2'-dihydroxy-4,4'-biphenyldicarboxylic acid

[0046] Mix 2,2'-dimethoxy-4,4'-biphenyldicarboxylic acid (1.10g, 3.6mmol), hydrobromic acid (4mL) and glacial acetic acid (10mL), stir and reflux at 125°C for 8 hours , cooled, filtered with suction, washed with water, and dried to obtain 2,2'-dihydroxy-4,4'-biphenyldicarboxylic acid (C 14 h 10 o 6 ) (0.90 g, 3.3 mmol), the yield was 91.2%.

[0047] 1 H NMR (d 6 -DMSO): δ7.54-7.57 (d, 2H), 7.65 (s, 2H), 7.72-7.75 (d, 2H); elemental analysis (C 14 h 10 o 6 ): theoretical value (%), C, 61.32; H, 3.67; found value (%) C, 61.16; H, 3.86. m / z: 275.2 (M+1).

Embodiment 3

[0048] Example 3: Preparation of 2,2'-diethoxy-4,4'-biphenyldicarboxylic acid

[0049] A, the preparation of 4-iodo-3-ethoxybenzoic acid

[0050] Iodine (13.96g, 55mmol) and KI (10.46g, 63mmol) were dissolved in 70mL of water, and under stirring, it was added dropwise to 3-ethoxybenzoic acid (5.53g, 33.3mmol) at a mass percent concentration of 27 % ammonia (75mL) solution, the time was controlled at 20 minutes, and then continued to stir for 40 minutes. Acidify with 36% hydrochloric acid, and separate the precipitate by suction filtration. The filtrate was extracted with ethyl acetate (70×3mL), the solid separated from the extract was combined with the precipitate obtained by suction filtration, washed with water, and recrystallized to give white crystals of 4-iodo-3-ethoxybenzoic acid (4.57g, 15.7mmol) , yield 47.1%.

[0051] 1 H NMR (d 6 -DMSO): 1.29-1.33 (t, 3H), 3.90-3.97 (q, 2H), 7.35-7.39 (d, 1H), 7.47 (s, 1H), δ 7.73-7.75 (d, 1H).

[0052] The preparation of B, 4-...

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Abstract

The invention relates to a 2,2'-dialkoxyl-4,4'-biphenyl dioctyl phthalate compound and a synthesizing method thereof. The compound has a general formula as the right structure, wherein, R respectively represents -CH3, -CH2CH3 or -CH(CH3)2. The invention has the advantages of available reaction material and mild reaction condition, and is suitable for scale industrial production.

Description

technical field [0001] The invention relates to 2,2'-dialkoxy-4,4'-biphenyl dicarboxylic acid and its synthesis method. Background technique [0002] Metal-organic frameworks (MOFs: Metal-organic Frameworks) have become a research hotspot for scientists all over the world because of their wide application in heterogeneous catalysis, separation, adsorption, gas storage and ion exchange. The commonly used ligands for the synthesis of MOFs materials are 4,4'-bipyridyl and biphenyl dicarboxylic acid compounds. And 2,2'-dialkoxy-4,4'-biphenyl dicarboxylic acid, such as 2,2'-dihydroxy-4,4'-biphenyl dicarboxylic acid, 2,2'-dimethoxy- 4,4'-biphenyl dicarboxylic acid, etc., all belong to biphenyl dicarboxylic acid, which can be used as a ligand to synthesize multifunctional MOFs materials. [0003] But 2,2'-dimethoxy-4,4'-biphenyl dicarboxylic acid, 2,2'-diethoxy-4,4'-biphenyl dicarboxylic acid and 2,2'-diisopropoxy None of the base-4,4'-biphenyldicarboxylic acid has been reported...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C65/24C07C51/347
Inventor 朱敦如包魏魏王晓珠沈旋
Owner NANJING TECH UNIV
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