A kind of process method for preparing 5-bromoisochroman-4-one without catalyst method

A process method, the technology of isochroman, which is applied in the field of preparation of chemical raw materials, can solve the problems of high production cost of isochroman-4-one, unfavorable large-scale production and use, and difficulty in purification of finished compounds, so as to reduce production cost, Reduced production costs and cheap raw materials

Inactive Publication Date: 2020-11-10
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the price of these catalysts or additives is higher, so that the production cost of isochroman-4-one is higher, which is not conducive to large-scale production and use
At the same time, the existence of the catalyst in the reaction system will also cause difficulties in the purification of the finished compound, and cause more waste in the reaction environment solvent, which cannot be recycled.

Method used

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  • A kind of process method for preparing 5-bromoisochroman-4-one without catalyst method
  • A kind of process method for preparing 5-bromoisochroman-4-one without catalyst method
  • A kind of process method for preparing 5-bromoisochroman-4-one without catalyst method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take 2 mL of cyclohexane, 0.5 mmol of 5-bromoisochroman, and a magnetron into a high-pressure reactor with a polytetrafluoroethylene liner, and then pass oxygen into the reactor until the pressure of the oxygen in the reactor is Then, seal the reaction kettle, put it into a heating tank with a temperature of 140° C., and carry out the reaction for 20 h under the condition of magnetic stirring. After the reaction was completed, the reaction system was cooled to room temperature, and then, the internal standard quantitative analysis of the obtained product was carried out using a gas chromatograph, and the yield of 5-bromoisochroman-4-one was measured to be 87%. Afterwards, the product is separated and purified by column chromatography to obtain the finished product of 5-bromoisochroman-4-one. use 1 H-NMR, 13 C-NMR confirms the structure of the product in the appendix figure 1 And attached figure 2 .

Embodiment 2

[0028] Take 2 mL of n-hexane, 0.5 mmol of 5-bromoisochroman, and magnetons into a high-pressure reactor with a polytetrafluoroethylene liner, and then pass oxygen into the reactor until the pressure of oxygen in the reactor is 0.5 MPa, then, seal the reaction kettle, put it into a heating tank with a temperature of 140° C., and carry out the reaction for 20 h under the condition of magnetic stirring. After the reaction was completed, the reaction system was cooled to room temperature, and then, the internal standard quantitative analysis of the obtained product was carried out using a gas chromatograph, and the yield of 5-bromoisochroman-4-one was measured to be 82%. Afterwards, the product is separated and purified by column chromatography to obtain the finished product of 5-bromoisochroman-4-one.

Embodiment 3-8

[0030] Change the oxygen pressure in Example 2 to 0.2MPa, 0.7MPa, 1MPa, 1.5MPa, 2MPa, 3MPa, and other conditions remain unchanged to obtain the productive rate of 5-bromoisochroman-4-one product (gas phase internal standard) They were 43%, 81%, 65%, 61%, 67%, and 49%, respectively.

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Abstract

The invention provides a technical method for preparing 5-bromoisochroman-4-one through a catalyst-free process. The technical method comprises the following steps: dissolving 5-bromoisochroman into an organic solvent; introducing oxygen into the organic solvent; and sealing a reactor, and carrying out a reaction at a high temperature; wherein the organic solvent is selected from the group consisting of n-hexane, n-heptane, n-octane and cyclohexane; the introduction amount of the oxygen is that the pressure of the oxygen in the reactor is 0.2 to 3 MPa; the temperature of the reaction is 120 to180 DEG C; and the time of the reaction is 2 to 40 h. According to the invention, the 5-bromoisochroman-4-one is prepared by using the 5-bromoisochroman and the oxygen as raw materials under the condition of no addition of any catalysts or additives. The method provided by the invention has the following advantages: generation of wastes in the production process is reduced; a finished product iseasier to be purified; the purity of the product is significantly improved; a reaction solvent can be recycled; thus, the cost of production is reduced; and environmental pollution is reduced.

Description

technical field [0001] The invention relates to the technical field of preparation of chemical raw materials, in particular to a process for preparing 5-bromoisochroman-4-one without a catalyst. Background technique [0002] Isochroman-4-one and its derivatives have the effects of lowering blood pressure, treating Alzheimer's disease, anti-inflammation, and anti-oxidation, and are widely used in the field of medicine ( Studies in Natural Products Chemistry , 1995, 15 , 381–422). Isochroman-4-ones and their derivatives can be efficiently synthesized by oxidation of the carbon-hydrogen bond in isochroman. In the early days, the oxidants used were usually sodium hypochlorite, tert-butyl hydroperoxide, transition metal oxides, etc. However, these oxidants have problems such as high cost and large pollution. Compared with these oxidants, oxygen is more favored by the industry. It not only has a lower cost, but also produces water as a by-product after oxidation, which has lit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/76
CPCC07D311/76
Inventor 田欣哲建方方任运来王键吉申振鹏程新强任超群
Owner HENAN UNIV OF SCI & TECH
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