Preparation method of DMP (Dess-Martin periodinane)

A technology of oxidizing agent and high boiling point solvent is applied in the field of pharmaceutical chemical synthesis, which can solve the problems of reducing the amount of acetic anhydride, low yield, etc., and achieve the effects of simple and stable operation, high purity and easy product.

Active Publication Date: 2018-12-21
SHANGHAI ZAIQI BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the literature of this step, acetic acid and a large excess of acetic anhydride are used to react, and the yield after treatment is on the low side; or the temp

Method used

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  • Preparation method of DMP (Dess-Martin periodinane)
  • Preparation method of DMP (Dess-Martin periodinane)
  • Preparation method of DMP (Dess-Martin periodinane)

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Experimental program
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Effect test

Embodiment 1

[0035] 2-Iodobenzoic acid (50.0 g, 0.20 mol) was added to sulfolane (250 mL), and the solution was heated to 50°C. 90% of the above solution was slowly added dropwise to an aqueous solution (300 mL) of potassium hydrogen persulfate (147.4 g, 0.24 mol, 1.2 eq) at 50°C, and the reaction was incubated for 3 hours. Then the reaction solution was heated to 95° C. and the remaining 10% 2-iodobenzoic acid solution was slowly added dropwise to the reaction solution, and the reaction was continued for 3 hours. After the reaction was complete, it was cooled to 5°C and stirring was continued at this temperature for 1.5 hours. Add 1L of water under stirring, filter (the filtrate is to be recycled), the filter cake is rinsed with water and acetone successively, and dried at room temperature for 16 hours to obtain 53.2 g of 2-iodoxybenzoic acid (yield 95.04%), a white solid, and the purity of IBX is 99.7 % (confirmed by NMR and HPLC). The solid was determined to be IBX by HNMR detection. ...

Embodiment 2

[0040] 2-Iodobenzoic acid (5kg, 20mol) was added to DMF (25L), and the solution was heated to 60°C. 85% of the above solution was slowly added dropwise to an aqueous solution (40L) of potassium hydrogen persulfate (22.1kg, 36mol, 1.8eq) at 60°C, and the reaction was incubated for 3 hours. The reaction was heated to 95° C. and the remaining 15% 2-iodobenzoic acid solution was slowly added dropwise to the reaction liquid, and the reaction was continued for 2 hours. After the reaction was complete it was cooled to 0°C and stirring was continued at this temperature for 1 hour. 100L of water was added under stirring, and after filtration, the filter cake was rinsed with water and acetone successively and dried at room temperature for 16 hours to obtain 4.51kg (yield 80.53%) of a white solid, and the purity of IBX was 99.8% (confirmed by NMR and HPLC). The standard spectrum is consistent.

[0041] Add IBX (4.5kg, 16mol) into a mixed solvent of acetic anhydride (5.88kg, 57.6mol) an...

Embodiment 3

[0043] 2-Iodobenzoic acid (50kg, 200mol) was added to dimethylsulfoxide (250L), and the solution was heated to 55°C. 90% of the above solution was slowly added dropwise to an aqueous solution (300 L) of potassium hydrogen persulfate (159.6 kg, 260 mol, 1.3 equiv) at 70°C. React at 70°C for 3 hours. The reaction was heated to 90° C., and the remaining 10% 2-iodobenzoic acid solution was slowly added dropwise to the reaction liquid, and the reaction was continued for 3 hours. After the reaction was complete it was cooled to 0°C and stirring was continued at this temperature for 2 hours. 1000L of water was added under stirring, and the filtered cake was rinsed with water and acetone successively and dried at room temperature for 16 hours to obtain 45.4kg of white solid (yield 81.07%). The purity of IBX was 99.8% (confirmed by NMR and HPLC). NMR and standard The spectra are consistent.

[0044] 2-iodylbenzoic acid (45kg, 160mol) was added to acetic anhydride (53.8kg, 528mol) an...

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Abstract

The invention discloses a preparation method of a DMP (Dess-Martin periodinane). The target product DMP is obtained through two steps of reactions with 2-iodobenzoic acid, potassium hydrogen persulfate, glacial acetic acid, acetic anhydride and the like as raw materials. The process is convenient and stable, the product is easy to separate and high in yield, the method is environmentally friendly,the comprehensive yield is 82% or above, the raw materials are cheap and easy to obtain, and industrial mass production is facilitated.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical synthesis, and in particular relates to a preparation method of Dess Martin oxidant. Background technique [0002] Dess-Martine oxidant is a white crystal with a melting point of 130-133°C. Dess-Martine oxidant (also known as Dess-Martine high iodine reagent, DMP for short) is a commonly used, mild and selective oxidizing agent. It is often used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Its advantages are mild reaction conditions, moderate speed, less dosage and simple post-treatment. Its preparation method can be obtained by oxidizing cheap o-iodobenzoic acid with potassium bromate in sulfuric acid solution of appropriate concentration to form a compound, and the compound is then treated with acetic anhydride to obtain Dess Martin oxidant. . [0003] The first step intermediate 2-iodoxybenzoic acid (abbreviated as IBX) is prepared, usually with o-iodoben...

Claims

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Application Information

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IPC IPC(8): C07D347/00
CPCC07D347/00
Inventor 李开孙鹏李超田贝贝
Owner SHANGHAI ZAIQI BIO TECH
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