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Method for synthesizing dibornyl oxalate by using borneol

A diborneol oxalate and borneol technology, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of difficulty in synthesizing borneol, lack of diborneol oxalate, etc., and achieve easy separation and purification, low operating cost, easy to obtain effect

Active Publication Date: 2014-08-20
株洲松本药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] However, in the current research, due to the lack of diborneyl oxalate products, it is difficult to study the identification of bornyl oxalate in the intermediate of synthetic borneol and the content control method to improve the quality of synthetic borneol

Method used

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  • Method for synthesizing dibornyl oxalate by using borneol
  • Method for synthesizing dibornyl oxalate by using borneol
  • Method for synthesizing dibornyl oxalate by using borneol

Examples

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Effect test

Embodiment 1

[0044] With 7.5g (0.049mol) borneol (natural borneol, commercially available item, through recrystallization purification, ) was dissolved in 134g of n-hexane, reacted with 21.0g (0.23mol, the ratio of the amount of borneol to borneol was 4.8) anhydrous oxalic acid under the action of 3.1g boron anhydride catalyst for 25h at 55°C, and filtered to remove unreacted anhydrous oxalic acid Water oxalic acid and catalyst, and washed with water below 30°C for 5-6 times, the upper liquid was removed by rotary evaporation to remove most of the solvent, and then the unreacted raw material borneol was removed by steam distillation to obtain the crude product of dibornyl oxalate , and then use any one of acetone, ethanol, ethyl acetate, n-hexane, cyclohexane, etc. to obtain 1.5 g of dibornyl oxalate (0.0041 mol, the yield of the substance is 16.8%) through repeated recrystallization.

Embodiment 2

[0046] Dissolve 19.5g (0.13mol) borneol in 268.2g n-hexane, and mix with 55.5g (0.62mol, the ratio of borneol to 4.7) anhydrous oxalic acid under the action of 7.3g boron anhydride catalyst at 54-56 The reaction was carried out at °C for 115 h, and other conditions and operations were the same as those in Example 1 to obtain 8.2 g (0.0226 mol, yield of substance: 34.8%) of dibornyl oxalate.

Embodiment 3

[0048] 10.0g (0.065mol) borneol was dissolved in 91g cyclohexane and 69g light petroleum ether, and 8.6g (0.096mol, the ratio of the substance amount to borneol was 1.5) anhydrous under the action of 1.5g boric anhydride catalyst Oxalic acid was reacted at 60° C. for 24 h, and other conditions and operations were the same as in Example 1 to obtain 1.3 g of diborneyl oxalate (0.0036 mol, the yield of the substance was 11.0%).

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Abstract

The invention discloses a method for synthesizing dibornyl oxalate by using borneol. The method comprises the following steps: dissolving borneol into a certain amount of organic solvent; reacting with anhydrous oxalic acid at a certain temperature for certain time in the presence of the catalysts such as boric oxide, pyroboric acid or metaboric acid or titanium sulfate and metatitanic acid; filtering to remove the catalysts and unreacted anhydrous oxalic acid; washing with water many times; distilling the upper-layer liquid to remove the organic solvent to obtain a crude product; and performing water vapor distillation, recrystallization and the like to remove the unreacted raw material borneol, thus obtaining dibornyl oxalate. The raw material borneol comprises d-borneol, l-borneol and dl-borneol. In the reaction, the organic solvents such as aromatic hydrocarbon and branched paraffin can be used as reaction media. With a conventional heating process, the method disclosed by the invention has the advantages of mild conditions, simplicity in operation, easy separation of raw material from product, few side reactions and high product yield.

Description

technical field [0001] The invention relates to a method for synthesizing diborneol oxalate from borneol (including d-borneol, levoborneol and racemic borneol). Background technique [0002] Turpentine is a kind of natural essential oil with unique aroma obtained from pine resin secreted by pine trees through water vapor distillation. my country has abundant turpentine resources, and its annual output ranks first in the world. The main components of turpentine are α-pinene and β-pinene. Pine massoniana turpentine also contains a small amount of longifolene and caryophyllene. Therefore, turpentine can provide a C10 or C15 molecular skeleton, and at the same time provide multiple rings, bridge rings, and rings. Active structures such as external or internal double bonds have very high chemical reactivity, and are rare natural chemical synthesis raw materials, which are of great significance in the synthesis of spices and other functional substances [Zhao Zhendong, Liu Xianzhan...

Claims

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Application Information

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IPC IPC(8): C07C69/36C07C67/08
CPCC07C67/08C07C69/36
Inventor 田新庭赵振东张平辉袁晓敏刘晓辉徐士超雷腊王婧张瑞华陈玉湘
Owner 株洲松本药业有限公司
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