Synthetic method of camphorquinone

A synthetic method and technology of camphorquinone, applied in the field of camphorquinone synthesis, can solve problems such as high cost and complex process, achieve low production cost, simplify synthetic route, and broaden the application range

Inactive Publication Date: 2010-03-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction conditions are mild, but the disadvantage is that selenium compounds are still used
[0022] Taking a comprehensive view of the existing literature reports, the current methods for synthesizing camphorquinone mainly use camphor as the starting material, and

Method used

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  • Synthetic method of camphorquinone
  • Synthetic method of camphorquinone
  • Synthetic method of camphorquinone

Examples

Experimental program
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Example Embodiment

[0038] Example 1:

[0039] Add 28g (0.2mole) α-pinene and 50ml n-hexane into a 250ml four-neck flask equipped with a thermometer, agitator, drying tube and HCl absorption device, and cool to the system temperature at -5~0℃ in an ice-salt bath . Weigh 117g (2mole) of sodium chloride into a 250ml three-necked flask, drop 53.3ml (1mole) of concentrated sulfuric acid with a constant pressure dropping funnel, and pass the generated HCl gas into α-pinene after being dried by anhydrous chlorine CaCl2 In the n-hexane solution, the reaction is about 8h, until the HCl gas is no longer absorbed. The obtained reaction solution was washed with 10% NaHCO3 solution to remove excess HCl, the organic layer was dried over anhydrous Na2SO4, and the n-hexane was evaporated under normal pressure to obtain the solid crude 2-chlorocamphane. Recrystallize with absolute ethanol (crude product: ethanol = 1:8-10g / ml) to obtain 31.7g of intermediate 2-chlorobornane, with a melting point of 129-131°C and a...

Example Embodiment

[0042] Example 2:

[0043] 28g (0.2mole) α-pinene and 50ml n-hexanepentane were added to a 250ml four-neck flask equipped with a thermometer, agitator, drying tube and HCl absorption device, and dried HCl gas was introduced at room temperature to react for 6h. The resulting reaction solution uses 10% NaHCO 3 The solution was washed to remove excess HCl, and the organic layer was treated with anhydrous Na 2 SO 4 After drying and evaporating the n-pentane under normal pressure, a solid crude product of 2-chlorobornane is obtained. It was recrystallized with a small amount of n-hexane to obtain 20.5 g of intermediate 2-chlorobornane. Dissolve 25.2g (0.2mole) potassium n-pentoxide in 100ml DMF, heat to 135℃, and add 2-chlorobornane-DMF solution (17.3g (0.1mole) 2-chlorobornane into 50ml using a dropping funnel) DMF), react at this temperature for 4h. After the reactants are cooled, add 100ml of water and extract 3 times with 100ml of n-hexane. The extract is washed with water until ...

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Abstract

The invention relates to a synthetic method of camphorquinone, which comprises the following steps: enabling a raw material alpha-pinene and dry chlorine hydride gas to react at -5-35 DEG C for 5-10 hours; washing the obtained reaction liquid with a 10% NaHCO3 solution, and removing the excessive HCl; drying an organic layer with anhydrous Na2SO4; steaming to remove the solvent at normal pressureto obtain a solid crude product 2-chlorocamphane; recrystallizing to obtain an intermediate 2-chlorocamphane; removing the chlorine hydride from the 2-chlorocamphane to obtain bornylene; using potassium permanganate as an oxidant, and carrying out oxidation reaction at the temperature of -15-35 DEG C for 3-24 hours; removing the byproduct MnO2 from the reaction liquid by centrifugation; after removing acetone from the solution by distillation, adding ethyl acetate for dissolving; washing with distilled water to remove the potassium permanganate; and after drying the organic layer by the anhydrous Na2SO4, steaming to remove the solvent to obtain yellow crystal camphorquinone. The invention has the advantages that the production cost of the camphorquinone is reduced, the application range ofthe camphorquinone is widened, and the production safety is improved.

Description

Technical field: [0001] The invention relates to a method for synthesizing camphorquinone. Using α-pinene as raw material, add dry HCl and isomerize to obtain 2-chlorobornane, and then remove HCl to obtain norbornene, which is oxidized to obtain camphorquinone. It belongs to the technical field of fine organic synthesis and drug synthesis. [0002] Background technique: [0003] Camphorquinone, also known as Ciquinone, the chemical name is 1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione, the English name is camphorquinone; 1,7,7-trimethyl -bicyclo[2.2.1]heptane-3-dione; bornane-2,3-dione; molecular formula C 10 h 14 o 2 , with a molecular mass of 166.21, is a bicyclic monoterpenoid compound, a yellow crystal, with a melting point of 196-196.5°C and a density of 2.9056g / cm 3 , the refractive index n 20 D 1.6380, slightly soluble in hot water, insoluble in cold water, soluble in ethanol, ether, benzene and other organic solvents. It is a commonly used chemical reage...

Claims

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Application Information

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IPC IPC(8): C07C49/433C07C45/28
Inventor 王石发杨益琴敖汪伟杨丽娟毕中保李好瑾刘兵杨杨
Owner NANJING FORESTRY UNIV
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