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Method for preparing 6-hydroxyl-6 (hydroxymethyl)-2H-pyran-3(6H)-one through catalytic oxidation

A hydroxymethyl, catalytic oxidation technology, applied in organic chemistry and other directions, can solve problems such as unsatisfactory yield, lower green index, etc., and achieve the effects of low cost, high yield and mild reaction conditions

Active Publication Date: 2021-06-08
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the reaction system usually requires an organic solvent, which reduces the "green index" of the reaction, and the 6-hydroxyl-6(hydroxymethyl)-2H-pyran-3(6H)-one obtained by ball milling under solvent-free conditions The yield is not ideal, only 45%-63% (Synth. Commun., 2015, 45, 348–354)

Method used

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  • Method for preparing 6-hydroxyl-6 (hydroxymethyl)-2H-pyran-3(6H)-one through catalytic oxidation
  • Method for preparing 6-hydroxyl-6 (hydroxymethyl)-2H-pyran-3(6H)-one through catalytic oxidation
  • Method for preparing 6-hydroxyl-6 (hydroxymethyl)-2H-pyran-3(6H)-one through catalytic oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 2,5-furandimethanol (0.05g, 5g / L), titanium silicon molecular sieve TS-1 (Si / Ti molar ratio is 30:1, 0.1g), H 2 o 2 (30wt%, 0.06mol / L) add 10mL H 2 O, and stirred at 30°C for 30 min. After cooling, take 5mL of the reaction solution and settle it into a 100mL volumetric flask, and carry out HPLC measurement after passing through a 0.22 μm microporous membrane. The conversion rate of 2,5-furandimethanol is 100%. The yield of methyl)-2H-pyran-3(6H)-one (structural formula shown below) is 95.2%, see figure 1 As shown, the product was in the form of a yellow oil.

[0042]

[0043] The nuclear magnetic characterization data of the product 6-hydroxyl-6(hydroxymethyl)-2H-pyran-3(6H)-one is: 1H-NMR (400MHz, CDCl 3 ): δ=6.84(d,1H), 6.20(d,1H), 4.63(d,1H), 4.18(d,1H), 3.82(d,1H), 3.65(d,1H).

Embodiment 2-5

[0045] Other processing conditions and reaction steps are the same as in Example 1, but using different reaction temperatures, the results are shown in Table 1.

[0046] Table 1. Experimental results of catalytic conversion of 2,5-furandimethanol by titanium-silicon molecular sieves at different reaction temperatures

[0047]

Embodiment 6-8

[0049] Other processing conditions and reaction steps are the same as in Example 1, but using different reaction times, the results are shown in Table 2.

[0050] Table 2. Experimental results of catalytic conversion of 2,5-furandimethanol by titanium-silicon molecular sieves under different reaction times

[0051]

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Abstract

The invention discloses a method for preparing 6-hydroxyl-6(hydroxymethyl)-2H-pyran-3(6H)-one through catalytic oxidation. The method comprises the following steps: taking a titanium silicalite molecular sieve as a catalyst, hydrogen peroxide as an oxidant and water as a reaction medium, carrying out catalytic oxidation on 2,5-furan dimethanol at 15-100 DEG C for 20-120 minutes, thereby preparing 6-hydroxyl-6 (hydroxymethyl)-2H-pyran-3(6H)-one. 6-hydroxyl-6(hydroxymethyl)-2H-pyran-3(6H)-one is obtained through a one-step catalytic oxidation process under mild conditions, a cleaner and more economical catalytic process is realized, the yield is as high as 95.2%, the cost is low, few byproducts are produced, the method is environment-friendly, the atom economy and the reaction efficiency are relatively high, the product is easy to separate, and the method has a good industrial application prospect.

Description

technical field [0001] The invention relates to a method for preparing bioactive molecule 6-hydroxy-6(hydroxymethyl)-2H-pyran-3(6H)-one by catalyzing and oxidizing 2,5-furandimethanol with titanium-silicon molecular sieve under mild and green conditions , belongs to the technical field of chemical synthesis. Background technique [0002] With the increasing consumption of fossil resources and increasingly severe environmental pollution, biomass and its derivatives are functionalized through various reaction pathways (such as oxidation, reduction, amination, etc.), and are gradually used in modern organic synthesis and bulk and fine In the industrial production of chemicals, they are expected to be sustainable alternatives to petroleum-based chemicals. Among them, the Achmatowicz rearrangement reaction is a kind of epoxidation oxidation reaction, which can oxidize furan derivatives (alkyl-substituted furan, furfuryl alcohol, alkyl-substituted furfuryl alcohol, etc.) into mor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/32
CPCC07D309/32
Inventor 张建郝盼盼李振宇韩莹莹
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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