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Preparation and recovery method of 2-methyl-5-iodobenzoic acid

A technology of o-toluic acid and iodobenzoic acid is applied in the field of preparation and recovery of 2-methyl-5-iodobenzoic acid, and can solve problems such as being unsuitable for industrial production, long reaction process, complicated handling and the like

Active Publication Date: 2014-01-29
ABA CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has a long reaction process and is cumbersome to handle, so it is not suitable for industrial production.

Method used

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  • Preparation and recovery method of 2-methyl-5-iodobenzoic acid
  • Preparation and recovery method of 2-methyl-5-iodobenzoic acid
  • Preparation and recovery method of 2-methyl-5-iodobenzoic acid

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Experimental program
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Effect test

Embodiment 1

[0026] Synthesis of 2-methyl-5-iodobenzoic acid

[0027] 500ml reaction bottle, nitrogen protection, add acetic acid (200g), water (20g), concentrated sulfuric acid (20g) at room temperature, stir and mix well, then add o-toluic acid (49g, 0.36mol), potassium persulfate (50g) in sequence , finally add iodine (38g, 0.15mol), the temperature of the solution rises slightly, after stirring for 30 minutes, slowly raise the temperature to 50°C, and keep it for 1 hour; then slowly raise the temperature to 70°C, keep it for 2 hours; -4 hours, the color of iodine in the reaction solution gradually disappeared, and the reaction solution was pale yellow. Reaction liquid sampling HPLC analysis (o-toluic acid ~ 10%; 2-methyl-5-iodobenzoic acid ~ 75%; 2-methyl-3-iodobenzoic acid ~ 15%; 2-methyl-3, 5-Diiodobenzoic acid <1%).

[0028] The reaction was stopped, and the reaction solution was slowly cooled to 15-20°C, filtered, washed, and dried to obtain ~55g of crude product (yield 70%, calc...

Embodiment 2

[0035] Synthesis of 2-methyl-5-iodobenzoic acid

[0036] 500ml reaction bottle, under nitrogen protection, add propionic acid (200g) and water (20g) at room temperature and mix well, then add concentrated sulfuric acid (20g), o-toluic acid (49g, 0.36mol), potassium persulfate (50g) in sequence , finally add iodine (38g, 0.15mol), the temperature of the solution rises slightly, after stirring for 30 minutes, slowly raise the temperature to 50°C, and keep it for 1 hour; then slowly raise the temperature to 70°C, keep it for 2 hours; -4 hours, the color of iodine in the reaction solution gradually disappeared, and the reaction solution was light yellow. Reaction liquid sampling HPLC analysis (o-methylbenzoic acid ~ 8%; 2-methyl-5-iodobenzoic acid ~ 80%; 2-methyl-3-iodobenzoic acid ~ 11%; 2-methyl-3, 5-Diiodobenzoic acid <1%).

[0037] The reaction was stopped, and the reaction solution was slowly cooled to 15-20°C, filtered, washed, and dried to obtain ~58.9 g of crude product ...

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Abstract

The invention provides a preparation and recovery method of 2-methyl-5-iodobenzoic acid. The method comprises the steps: iodinating by using iodine / potassium periodate in a mixed acid solvent and taking otoluic acid as a raw material to obtain a mixture of 2-methyl-5-iodobenzoic acid, 2-methyl-3-iodobenzoic acid and 2-methyl-3, 5-diiodosalicylic acid; refining to obtain 2-methyl-5-iodobenzoic acid and a mother solution regenerant, wherein the mother solution regenerant is the mixture of 2-methyl-5-iodobenzoic acid, 2-methyl-3-iodobenzoic acid and 2-methyl-3, 5-diiodosalicylic acid; recovering otoluic acid and iodine ions through catalytic hydrogenation deiodination; oxidizing the iodine ions for recovering iodine. The whole process is circularly utilized. The preparation and recovery method has the advantages that the raw material is easy to obtain and low in price, the preparation process is simple in operation, the equipment requirement is low, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for preparing and recovering 2-methyl-5-iodobenzoic acid. Background technique [0002] 2-Methyl-5-iodobenzoic acid is an important intermediate in some new diabetes drugs SGLT2, so it is of great significance to study its preparation method suitable for industrial production. [0003] Its synthesis is reported in the literature, and there are mainly two schemes: [0004] (1) Direct iodination method [0005] [0006] JP4332702; JMC, 52(16), 5228-5240, 2009, WO2005003073, etc. The main problem of this type of method is the direct iodination method, there are a large number of 3-position iodine substitution impurities, and the refining loss is quite large. [0007] (two) diazotization iodide method [0008] [0009] The main literatures include: Bioorganic & Medicinal Chemistry Letter, 18(23):6273-8, 2008; WO2006177669, etc. The method has a long reaction process and complicated handling, and is not suitable ...

Claims

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Application Information

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IPC IPC(8): C07C63/70C07C51/363
CPCC07C51/363C07C63/70
Inventor 林志刚李航徐军阙利民秦东光江岳恒
Owner ABA CHEM CORP
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