Method for preparing 1, 8-dialkoxy-1, 3, 6, 8-tetraalkoxy-2, 7-dimethyl-4-octylene

A technology of tetraalkoxy and dialkoxy, which is applied in the field of organic synthesis, can solve the problems of large environmental pollution, high production cost, corrosion, etc., and achieve the effect of simple post-processing and improved reaction yield

Active Publication Date: 2021-11-05
WANHUA CHEM GRP CO LTD
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Problems solved by technology

In this process, strong acids and strong oxidants are used, which puts high demands on the production equipment, resulting in high industrial production costs
[0005] Chinese patent CN100460378C discloses a method for preparing 2,7-dimethyloctane-2,4,6-trienedialdehyde, which uses butenedialdehyde diacetal and enol ether as raw materials, and double The enol ether is condensed to form an addition product. The problem of this process is that the post-treatment operation of the Lewis acid catalyst is cumbersome, the environmental pollution is relatively large, and the problem of equipment corrosion cannot be ignored.
[0006] In summary, although there are many methods for preparing dedecenal intermediates in the prior art, it is difficult to realize industrialization due to pollution or corrosion problems. Therefore, a reasonable method for preparing 1,8-dialkoxy- The method of 1,3,6,8-tetraalkoxy-2,7-dimethyl-4-octene will greatly improve the shortcomings of the existing dedecenal intermediate synthesis technology and realize the improvement of benefits

Method used

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  • Method for preparing 1, 8-dialkoxy-1, 3, 6, 8-tetraalkoxy-2, 7-dimethyl-4-octylene
  • Method for preparing 1, 8-dialkoxy-1, 3, 6, 8-tetraalkoxy-2, 7-dimethyl-4-octylene
  • Method for preparing 1, 8-dialkoxy-1, 3, 6, 8-tetraalkoxy-2, 7-dimethyl-4-octylene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Preparation of a 1,1,3,6,8,8-hexamethoxy-2,7-dimethyl-4-octene

[0038] Add 0.1mol (17.9g) 1,1,4,4-tetramethoxy-2-butene, 0.21mol (15.2g) propenyl methyl ether, 0.01mol (1.66g) potassium iodide, 0.33 g tetraethylammonium hexafluorophosphate and 178.8 g solvent (143.0 g ethyl acetate and 35.8 g water). Two graphite rods (Φ5mm) were used as anode and cathode respectively. Pass the reaction mixture through 50mA / cm 2 The electric current, stirred at 20 ℃ for 6.0h. After the reaction is completed, add it to a separatory funnel and let it stand for stratification, and the organic phase rotary evaporator will remove the solvent to obtain 1,1,3,6,8,8-hexamethoxy-2,7-dimethyl -4-octene product, the reaction conversion rate is 95.0%, the selectivity is 98.3%, and the reaction yield is 93.4%.

[0039] The H NMR spectrum of 1,1,3,6,8,8-hexamethoxy-2,7-dimethyl-4-octene:

[0040] HNMR (DMSO, 400 MHz) δ = 1.53 (s, 6H), 2.58 (s, 2H), 3.31 (s, 18H), 5.42 (s, 2H), 6.88 (...

Embodiment 2

[0041]Example 2: Preparation of a 1,8-diethoxy-1,3,6,8-tetramethoxy-2,7-dimethyl-4-octene

[0042] Add 0.1mol (17.9g) 1,1,4,4-tetramethoxy-2-butene, 0.23mol (19.8g) propenyl ethyl ether, 0.005mol (0.75g) sodium iodide, 0.37 g tetraethylammonium hexafluorophosphate and 178.8 g solvent (158.9 g methanol and 19.9 g water). Two graphite rods (5 mm in diameter) were used as anode and cathode, respectively. Pass the reaction mixture through 100mA / cm 2 The electric current, stirred at 30 ℃ for 4.0h. After the reaction is completed, add it to a separatory funnel and let it stand for stratification, and remove the solvent with a rotary evaporator for the organic phase to obtain 1,8-diethoxy-1,3,6,8-tetramethoxy-2 , 7-dimethyl-4-octene product, the reaction conversion rate is 94.6%, the selectivity is 96.3%, and the reaction yield is 91.1%.

Embodiment 3

[0043] Example 3: Preparation of a 1,1,3,6,8,8-hexamethoxy-2,7-dimethyl-4-octene

[0044] Add 0.2mol (35.7g) 1,1,4,4-tetramethoxy-2-butene, 0.5mol (36.0g) propenyl methyl ether, 0.04mol (6.64g) potassium iodide, 0.66 g tetraethylammonium hexafluorophosphate and 214.2 g solvent (194.7 g methanol and 19.5 g water). Two graphite rods (Φ5mm) were used as anode and cathode respectively. Pass the reaction mixture through 60mA / cm 2 The electric current, stirred at 50 ℃ for 2.0h. After the reaction is completed, add it to a separatory funnel and let it stand for stratification, and the organic phase rotary evaporator will remove the solvent to obtain 1,1,3,6,8,8-hexamethoxy-2,7-dimethyl -4-octene product, the reaction conversion rate is 93.5%, the selectivity is 96.4%, and the reaction yield is 90.1%.

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Abstract

The invention discloses a method for preparing 1, 8-dialkoxy-1, 3, 6, 8-tetraalkoxy-2, 7-dimethyl-4-octylene. The method comprises the following steps of: adding iodized salt, electrolyte, 1, 1, 4, 4-tetraalkoxy-2-butene, allyl alkyl ether and a solvent into a reaction container; and performing reaction under the condition of electrification to obtain the 1, 8-dialkoxy-1, 3, 6, 8-tetraalkoxy-2, 7-dimethyl-4-octylene. The method has the advantages of high efficiency, no use of a metal catalyst in the reaction, environmental protection and mild reaction conditions, and overcomes the defects of serious transition metal catalytic pollution, complex process, tedious post-treatment and the like in the prior art.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for preparing 1,8-dialkoxy-1,3,6,8-tetraalkoxy-2,7-dimethyl-4-octene by electrolysis method. Background technique [0002] 1,8-dialkoxy-1,3,6,8-tetraalkoxy-2,7-dimethyl-4-octene, is the preparation of decabisaldehyde (2,7-dimethyl- 2,4,6-Octatriene-1,8-dialdehyde) is an important precursor, and ten-carbon dialdehyde is the key fragment of carotenoids, so it is found to effectively synthesize 1,8-dialkoxy -1,3,6,8-tetraalkoxy-2,7-dimethyl-4-octene method is of great significance for the efficient synthesis of carotenoids. [0003] Chinese patent CN101597220A discloses a method in which an alkali metal hydroxide or an alkali metal alkylate is immobilized on an effective carrier, added to the reaction system, and catalyzed with the assistance of a crown ether. This method enables the synthesis of 1,1,8,8- The yield of tetramethoxy-2,7-dimethyl-2,4,6-octatriene ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/07
CPCC25B3/07
Inventor 王嘉辉张涛沈宏强刘英瑞张弈宇罗朝辉宋军伟
Owner WANHUA CHEM GRP CO LTD
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