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Method for synthesizing diisoborneol oxalate

A technology for synthesizing diisobornyl oxalate and diisobornyl oxalate, which is applied to the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, and can solve the lack of synthetic methods for diisobornyl oxalate products , Difficulty in synthesizing borneol, etc., to achieve the effect of easy purification, easy acquisition, and low operating cost

Active Publication Date: 2014-08-13
株洲松本药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] However, in the current research, due to the lack of relatively pure diisobornyl oxalate products and effective synthesis methods, in order to study the identification of isobornyl oxalate in the intermediate of synthetic borneol and the content control method to improve the quality of synthetic borneol bring difficulties

Method used

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  • Method for synthesizing diisoborneol oxalate
  • Method for synthesizing diisoborneol oxalate
  • Method for synthesizing diisoborneol oxalate

Examples

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Embodiment 1

[0045] Embodiment 1 (with industrial camphene as raw material)

[0046] With 10.3g (0.076mol) amphene (produced by Suzhou Youhe Technology Co., Ltd., its composition and content are: 77.0% amphene, 20.1% tricyclene, specific optical rotation ) was dissolved in 107.5g of light petroleum ether, reacted with 8.1g (0.090mol, the mass ratio of amphene to amphene: 1.18) of anhydrous oxalic acid under the action of 1.1g of boron anhydride catalyst for 72h, and filtered to remove The catalyst and unreacted oxalic acid were washed 5-6 times with water below 30°C, and the upper liquid was removed by rotary evaporation to remove most of the solvent, and then steam distillation was used to remove unreacted raw material camphene, tricycloene and a small amount of by-products. The product isoborneol is obtained thick product, then obtains diisoborneol oxalate 2.6g (0.0072mol, yield 19.0%) through repeated recrystallization with acetone, ethanol, ethyl acetate, normal hexane or hexanaphthen...

Embodiment 2

[0048] 29.0g (0.21mol) of camphene is dissolved in 190.0g of light petroleum ether, and 16.1g (0.18mol, the substance mass ratio with camphene is 0.84) of anhydrous oxalic acid under the action of 2.7g boron anhydride catalyst is at 55 ℃ After reacting for 85 hours, other conditions and operations were the same as in Example 1 to obtain 11.3 g (0.031 mol, yield 29.2%) of diisobornyl oxalate.

Embodiment 3

[0050] 11.0g (0.081mol) amphene was dissolved in 151.1g light petroleum ether, and 11.0g (0.12mol, the mass ratio with amphene was 1.51) anhydrous oxalic acid under the action of 0.7g boron anhydride catalyst at 55 ℃ After reacting for 191 h, other conditions and operations were the same as in Example 1, and 2.1 g (0.0058 mol, yield 14.2%) of relatively pure diisobornyl oxalate was obtained.

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Abstract

The invention discloses a method for synthesizing diisoborneol oxalate. The diisoborneol oxalate is prepared from such raw materials as industrial camphene, camphene, tricyclene and isoborneol. The method comprises the following steps: dissolving raw materials in a certain amount of an organic solvent, reacting with anhydrous oxalic acid at certain temperature for a certain duration in the presence of such catalysts as boron anhydrous, pyroboric acid or metaboric acid or titanium sulfate, or metatitanic acid, filtering and removing the catalysts and unreacted anhydrous oxalic acid, washing for several times, rotatably evaporating upper liquid to remove most solvents, removing camphene and tricyclene as raw materials which are not reacted completely as well as a few of isoborneol as a byproduct to obtain a crude product, and recrystallizing to obtain diisoborneol oxalate. The method disclosed by the invention can adopt such organic solvents as aromatic hydrocarbon and branched paraffin as reaction mediums in reaction. The method, which adopts conventional heating, is moderate in conditions, simple and convenient to operate, low in side reaction and high in product yield, and raw materials are easily separated from products.

Description

technical field [0001] The invention relates to a method for synthesizing diisoborneol oxalate, in particular to a method for synthesizing diisoborneol oxalate with camphene, tricyclene or isoborneol as raw materials. 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...

Claims

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Application Information

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IPC IPC(8): C07C69/36C07C67/04C07C67/08C07C67/00
CPCC07C67/00C07C67/04C07C67/08C07C2602/42C07C69/36
Inventor 赵振东张平辉田新庭徐士超袁晓敏刘晓辉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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