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Tetrahydropyrane-3-formic acid preparation method

A technology of tetrahydropyran and formic acid, which is applied in the direction of organic chemistry, can solve the problems of expensive silver nitrate, high cost, and unsuitability for industrial production, and achieve the effects of low production cost, mild chemical reaction conditions, and strong operability

Inactive Publication Date: 2013-12-04
ASCEPION PHARMA
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Problems solved by technology

But the silver nitrate used in this method is very expensive, and the cost is very high, so it is not suitable for industrial production

Method used

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  • Tetrahydropyrane-3-formic acid preparation method
  • Tetrahydropyrane-3-formic acid preparation method

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Embodiment Construction

[0020] The present invention will be described in detail below through specific embodiments, but the present invention is not limited to these examples.

[0021] Add 5L of water, 840mL of concentrated hydrochloric acid and 600mL of toluene into a 20L reaction kettle, add 1Kg of acrolein, heat to an internal temperature of 65-75 degrees under nitrogen protection, and react for about 2 hours. The reaction solution was cooled, filtered, and separated into layers. The toluene layer was neutralized with aqueous sodium bicarbonate until there were no bubbles, dried, and the solvent was removed by rotary evaporation to obtain a crude product. The aqueous layer was extracted with dichloromethane, 2.5 L / time, four times, the organic layers were combined, neutralized with aqueous sodium bicarbonate solution, dried, and the solvent was removed by rotary evaporation to obtain a crude product. The two crude products were combined and distilled under reduced pressure to obtain 5,6-dihydro-...

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Abstract

The present invention discloses a tetrahydropyrane-3-formic acid preparation method, wherein acrolein is adopted as a raw material, and the preparation method comprises the following three steps: (1) acrolein is subjected to a ring closure reaction under an acid effect to obtain 5,6-dihydro-2-H pyran-3-formaldehyde, (2) the 5,6-dihydro-2-H pyran-3-formaldehyde and hydrogen are subjected to a reduction reaction under a metal catalyst effect to obtain tetrahydropyrane-3 formaldehyde, and (3) the tetrahydropyrane-3 formaldehyde and a Jones reagent are subjected to an oxidation reaction to obtain tetrahydropyrane-3-formic acid.

Description

technical field [0001] The invention relates to a method for preparing tetrahydropyran-3-carboxylic acid from acrolein. Background technique [0002] Tetrahydropyran-3-carboxylic acid is an important pharmaceutical intermediate. Its structural formula is: [0003] [0004] Compounds having the tetrahydropyran ring as the central part of the molecule play an important role in organic chemistry, for example as components of natural or synthetic fragrance substances, pharmaceuticals or mesogenic or liquid crystal compounds, or as useful substances for the synthesis of these precursor. [0005] For example, tetrahydropyran-3-carboxylic acid is a good insect trap after esterification, and the report on this is: Bioscience, Biotechnology, and Biochemistry, 1994, vol.58, #10p.1879-1881. [0006] In the prior art, the preparation method of tetrahydropyran-3-carboxylic acid mainly contains the following 1 kind: [0007] 1) Using acrolein as a starting material, in toluene and ...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/08
Inventor 高小勇
Owner ASCEPION PHARMA
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