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Preparation method of p-vinylsalicylic acid

A technology of vinyl salicylic acid and p-aminosalicylic acid, which is applied in the field of preparation of p-vinyl salicylic acid, can solve the problems of unfavorable large-scale application, easy to be oxidized, and high price, and achieve industrial scale The effect of production, reducing the difficulty of post-processing, and streamlining the operation process

Active Publication Date: 2020-12-15
江苏美迪克化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Yet the 2-hydroxyl-4-iodobenzoic acid methyl ester that this method uses and vinylboric anhydride pyridine complex price are more expensive, and used catalyst Pd(PPh3)4 is easily oxidized and inactivated in the air, which is not conducive to large-scale industrial application

Method used

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  • Preparation method of p-vinylsalicylic acid
  • Preparation method of p-vinylsalicylic acid
  • Preparation method of p-vinylsalicylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Stir 5mmol (765mg) p-aminosalicylic acid and 7.5mmol (0.65mL) 36% concentrated hydrochloric acid at room temperature for 15min, cool to 0°C and slowly add 7.5mmol (518mg sodium nitrite dissolved in 2.2mL water) sodium nitrite aqueous solution dropwise Continue stirring for 15 min, then add 7.5 mmol (1.43 g) CuI in batches and continue stirring for 30 min at room temperature to generate p-iodosalicylic acid.

[0039] After the reaction, without post-treatment, the reaction solution was directly transferred to the hydrothermal reaction kettle, and 17.5mmol (700mg) NaOH, 0.05mmol (46mg) Pd were added to the reaction mixture 2 (dba) 3 , 10mmol (1.9g) of triethoxyvinylsilane and 5mL of methanol, the temperature was raised to 100°C and the reaction was continued for 10h. After cooling down, add 1M HCl to adjust the pH value to neutral, extract and separate the liquid, take the organic phase and dry it, remove the organic phase by rotary evaporation, and obtain p-vinyl salicy...

Embodiment 2

[0041] Stir 5mmol (765mg) p-aminosalicylic acid and 7.5mmol (0.65mL) 36% concentrated hydrochloric acid at room temperature for 15min, cool to 0°C and slowly add 7.5mmol (518mg sodium nitrite dissolved in 2.2mL water) sodium nitrite aqueous solution dropwise Stirring was continued for 15 min, and then 7.5 mmol (1.25 g KI was dissolved in 2.2 mL water) KI aqueous solution was slowly added dropwise and stirring was continued for 30 min at room temperature to generate p-iodosalicylic acid.

[0042] After the reaction, without post-treatment, the reaction solution was directly transferred to the hydrothermal reaction kettle, and 17.5mmol (700mg) NaOH, 0.05mmol (46mg) Pd were added to the reaction mixture 2 (dba) 3 , 10mmol (1.9g) of triethoxyvinylsilane and 5mL of methanol, the temperature was raised to 100°C and the reaction was continued for 10h. After cooling down, add 1M HCl to adjust the pH value to neutral, extract and separate the liquids, take the organic phase and dry it...

Embodiment 3

[0044] Stir 5mmol (765mg) p-aminosalicylic acid and 7.5mmol (0.65mL) 36% concentrated hydrochloric acid at room temperature for 15min, cool to 0°C and slowly add 7.5mmol (518mg sodium nitrite dissolved in 2.2mL water) sodium nitrite aqueous solution dropwise Stirring was continued for 15 min, and then 7.5 mmol (1.25 g KI was dissolved in 2.2 mL water) KI aqueous solution was slowly added dropwise and stirring was continued for 30 min at room temperature to generate p-iodosalicylic acid.

[0045] After the reaction was finished, the reaction liquid was directly transferred to the hydrothermal reaction kettle without post-treatment, and 17.5 mmol (700 mg) NaOH, 0.05 mmol (265 mg) 5% Pd / C, 10 mmol (1.9 g) Tris Ethoxyvinylsilane and 5mL of methanol were heated to 100°C to continue the reaction for 10h. After cooling down, add 1M HCl to adjust the pH value to neutral, extract and separate the liquid, take the organic phase to dry, remove the organic phase by rotary evaporation, obt...

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Abstract

The invention discloses a p-vinylsalicylic acid preparation method, which comprises: (1) carrying out a diazotization reaction on p-aminosalicylic acid and nitrous acid in water to generate a diazotization intermediate, and adding a metal iodide to carry out an iodination reaction to generate p-iodosalicylic acid; (2) reacting p-iodosalicylic acid with the compound shown in the formula (a) in a mixed solution of methanol and water to generate p-vinylsalicylic acid, wherein in the formula (a), R1, R2 and R3 are independently selected from C1-6 alkyl, C1-6 alkoxy, phenoxy, CH3 (CH2) mO (CH2) nO-, m is 0, 1, 2, 3, 4, 5 or 6, and n is 1, 2, 3, 4, 5 or 6; according to the method, ideal yield and purity can be obtained under mild and simple reaction conditions, side reactions are reduced, meanwhile, adopted reagent raw materials are cheaper and easier to obtain, and the method is safe, environmentally friendly and suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of p-vinyl salicylic acid. Background technique [0002] p-vinyl salicylic acid (4-ethenyl-2-hydroxybenzoic acid, or 4-vinyl salicylic acid, CASNo.: 71534-98-0, molecular formula C 9 h 8 o 3 ), its structural formula is: [0003] [0004] P-vinyl salicylic acid is an important synthetic intermediate, which can be used as a raw material for synthesizing a new type of photosensitizer, which has potential application value in the manufacture of dye-sensitized solar cells (Journal of Nanoscience and Nanotechnology 2016,16,4880- 4885), can also be used as a raw material for synthesizing novel cholinergic muscarinic M1 receptor modulators, and this M1 receptor modulator may be used as a preventive and therapeutic agent for Alzheimer's disease, schizophrenia, sleep disorders, Parkinson's disease, etc. Therapeutic drugs (WO2016208775A1). In additi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/19C07C51/353
CPCC07C51/353C07C51/363C07C65/19C07C65/05Y02E10/542
Inventor 杨盟徐肖洁景亚婷陆国刚
Owner 江苏美迪克化学品有限公司
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