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Method for preparing 8-hydroxyl caprylaldehyde

A technology of alkyl and octanediol, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, etc. It can solve the problems affecting the reaction and purification, and there will be double-sided acetylated by-products, so as to meet the reaction conditions Gentle, non-polluting yield effects

Inactive Publication Date: 2019-07-12
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires unilateral acetylation to protect the hydroxyl group, and there will be bilateral acetylated by-products and remaining raw materials, which will affect subsequent reactions and purification

Method used

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  • Method for preparing 8-hydroxyl caprylaldehyde
  • Method for preparing 8-hydroxyl caprylaldehyde
  • Method for preparing 8-hydroxyl caprylaldehyde

Examples

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Effect test

preparation example Construction

[0023] Preparation of composite catalyst (taking tetramethylethylenediamine and cuprous iodide as an example, the molar ratio is 1:1:1):

[0024] 30 grams (0.192mol) of Tempo, 22.3 grams (0.192mol) of tetramethylethylenediamine and 36.6 grams (0.192mol) of cuprous iodide were put into 70 milliliters of tetrahydrofuran solution and stirred for 1 hour, and the precipitate was filtered and at 45 °C after vacuum drying.

Embodiment 1

[0026] Add 5 grams (0.034mol) of 1,8-octanediol, 0.1 gram of composite catalyst (tetramethylethylenediamine, cuprous iodide and Tempo, molar ratio 1:1:1) and 20 mL of dry acetonitrile, the reaction mixture was stirred with air at room temperature, and the reaction was detected by TLC. After 24 hours of reaction, the reaction was completed, and the composite catalyst was removed by filtration (which can be recovered and reused), and the obtained filtrate was removed from the solvent. 4.65 g of liquid 8-hydroxyoctanal was obtained with a yield of 96.0% and a purity of 98.5% by gas phase analysis.

[0027] 1 HNMR (CDCl 3 , 400M), TMS): δ1.2-1.6 (m, 10H), 2.4 (t, 2H), 3.6 (t, 2H), 4.7 (s, br, 1H), 9.72 (s, 1H).

Embodiment 2

[0029] Add 10 grams (0.068mol) of 1,8-octanediol, 0.3 grams of composite catalyst (tetramethylethylenediamine, cuprous iodide and Tempo, molar ratio 1:1:1) and 40 mL of dry In acetonitrile, the reaction mixture was stirred with air at room temperature, and the reaction was detected by TLC. After reacting for 30 hours, the reaction was completed, and the composite catalyst was removed by filtration (which can be recycled), and the obtained filtrate was desolvated to obtain 9.5 grams of liquid 8-hydroxyoctanal, with a yield of 97.0% and a purity of 98.0% by gas phase analysis.

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Abstract

The invention discloses a method for preparing 8-hydroxyl caprylaldehyde and belongs to the field of chemical synthesis. The method comprises the steps of introducing air to 1,8-octanediol, which serves as a starting raw material, in a solvent at room temperature in the presence of a composite catalyst prepared from cuprous halide, substituted ethylenediamine and Tempo, carrying out a reaction forcertain time, then, carrying out filtering to remove the catalyst, and subjecting filter liquor to reduced-pressure distillation to remove the solvent, so as to obtain the product, i.e., the 8-hydroxyl caprylaldehyde. According to the method for preparing the 8-hydroxyl caprylaldehyde, disclosed by the invention, the technical line has the characteristics of short route, simplicity and convenience in operation and easiness in industrial production, and thus, the method for synthesizing the 8-hydroxyl caprylaldehyde is very economical, simple and convenient.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a preparation method of 8-hydroxyoctanal. Background technique [0002] 8-Hydroxyoctanal is an important intermediate in the synthesis of royal jelly acid. The chemical name of royal jelly acid is (E)-10-hydroxy-2-decenoic acid, referred to as 10-HDA. Because of its anti-bacterial, anti-cancer, anti-radiation and strong body and other physiological functions, it has attracted the attention of workers in the fields of chemistry, biology and medicine. [0003] Chinese patent application CN1280121A uses oleic acid as a starting material to synthesize royal jelly acid, and prepares intermediate 8-hydroxyoctylal from oleic acid through several steps. Its technological process is more complicated, is not suitable for industrialized production. [0004] Chinese patent application CN102010308A discloses a preparation method of 8-hydroxyoctanal, an intermediate for synt...

Claims

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Application Information

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IPC IPC(8): C07C45/38C07C47/19
CPCC07C45/38C07C47/19
Inventor 徐仁杰宗乾收姚鹏千芝妍周宏伟包琳
Owner JIAXING UNIV
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