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Synthetic method of camphorquinone

A synthetic method, a technology of camphorquinone, applied in the field of camphorquinone synthesis, can solve the problems of complicated process and high cost, and achieve the effects of simplifying the synthetic route, lowering the production cost and broadening the scope of application

Inactive Publication Date: 2012-09-05
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 various synthetic processes have different disadvantages, and their common features are high cost and complex technology. In the technical field, new synthetic routes are to be explored And synthetic method is one of the research directions of synthetic camphorquinone

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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Effect test

Embodiment 1

[0039] Add 28g (0.2mole) α-pinene and 50ml n-hexane into a 250ml four-neck flask equipped with a thermometer, stirrer, drying tube and HCl absorption device, and cool the system with an ice-salt bath until the system temperature is -5 to 0°C . Weigh 117g (2mole) of sodium chloride and place it in a 250ml three-necked flask, drop 53.3ml (1mole) of concentrated sulfuric acid into it with a constant pressure dropping funnel, and pass the generated HCl gas into α-pinene after being dried with anhydrous chlorine CaCl In n-hexane solution, react for about 8 hours until HCl gas is no longer absorbed. The resulting reaction solution was washed with 10% NaHCO3 solution to remove excess HCl, the organic layer was dried over anhydrous Na2SO4, and n-hexane was evaporated under normal pressure to obtain solid crude 2-chlorobornane. Recrystallized 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 an...

Embodiment 2

[0043] Add 28g (0.2mole) α-pinene and 50ml n-hexanepentane into a 250ml four-necked flask equipped with a thermometer, a stirrer, a drying tube and an HCl absorption device, and feed dry HCl gas at room temperature for 6 hours. The resulting reaction solution was treated with 10% NaHCO 3 solution washing to remove excess HCl, and the organic layer was washed with anhydrous Na 2 SO 4 After drying and distilling off n-pentane under normal pressure, the solid crude product 2-chlorobornane was obtained. Recrystallization was performed with a small amount of n-hexane to obtain 20.5 g of intermediate 2-chlorobornane. Dissolve 25.2g (0.2 mole) of potassium n-pentoxide in 100ml of DMF, heat to 135°C, and drop into the 2-chlorobornane-DMF solution with a dropping funnel (17.3g (0.1mole) of 2-chlorobornane is dissolved in 50ml DMF), reacted at this temperature for 4h, after the reactant was cooled, add 100ml of water, extracted 3 times with 100ml of n-hexane, the extract was washed w...

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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 of the 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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Patent Type & Authority Patents(China)
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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