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Method for synthesizing 2,7-dimethyl-octa-2,4,6-trienedial

A technology of octatriene and dimethyl, applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problem of high cost of triethyl phosphite, short reaction steps, and long process flow and other problems, to achieve the effects of convenient operation, high total yield and simple process

Active Publication Date: 2008-08-06
ZHEJIANG UNIV +1
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Problems solved by technology

[0002] 2,7-Dimethyl-2,4,6-octatriene-1,8-dialdehyde, melting point 157-159°C, stable at room temperature, easily soluble in ethanol, petroleum ether, slightly soluble in water, is a synthetic The key intermediate of carotenoids has important applications in the synthesis of β-carotene, canthaxanthin and astaxanthin, and its synthesis has not been reported in domestic literature
[0008] Although the reaction steps are short, the disadvantage is that the reaction yield is low, and the relatively high cost of triethylphosphonite has a special smell
[0011] As can be seen from the reaction formula, the preparation process of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde is long, there are seven steps of reaction, and the various auxiliary materials used are also relatively Many, complex process

Method used

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  • Method for synthesizing 2,7-dimethyl-octa-2,4,6-trienedial
  • Method for synthesizing 2,7-dimethyl-octa-2,4,6-trienedial
  • Method for synthesizing 2,7-dimethyl-octa-2,4,6-trienedial

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Embodiment 1

[0022] Add 300ml of tetrahydrofuran, 12.0g of magnesium powder, 2.1ml of trans-1,4-dichloro-2-butene with a gas phase content of 99.0%, and 0.1g of iodine into the reactor, heat, control the reaction temperature to 30°C, drop Add 11.3ml of trans-1,4-dichloro-2-butene with a gas phase content of 99.0%, dropwise, heat up to 40°C, keep the temperature for 2 hours, add dropwise 100ml of dimethoxyacetone containing 29.5g Tetrahydrofuran solution, after dripping, heat preservation reaction for 6 hours, cooled to 20°C to obtain the reaction solution; added the reaction solution dropwise to 150ml of dilute sulfuric acid with a concentration of 10% by weight for hydrolysis, the hydrolysis temperature was 0°C, continued to stir for 0.5 hours, and heated up To 30°C, remove tetrahydrofuran under reduced pressure, add 100ml of water, filter, wash the filter cake with water, and dry in vacuum to obtain 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde.

Embodiment 2

[0024] Add 300ml of tetrahydrofuran, 12.0g of magnesium powder, 4.2ml of trans-1,4-dichloro-2-butene with a gas phase content of 99.0%, and 0.1g of iodine into the reactor, heat, control the reaction temperature to 35°C, drop Add 22.6ml of trans-1,4-dichloro-2-butene with a gas phase content of 99.0%, dropwise, heat up to 60°C, keep the temperature for 5 hours, add dropwise 400ml of tetrahydrofuran containing 295g of dimethoxyacetone solution, dripping is completed, heat preservation reaction for 12 hours, cooled to 40 ℃ to obtain the reaction solution; the reaction solution is added dropwise to 600ml weight percent concentration and hydrolyzed in 20% dilute hydrochloric acid, the hydrolysis temperature is 20 ℃, continue to stir for 2 hours, and heat up to 50°C, remove tetrahydrofuran under reduced pressure, add 600ml of water, filter, wash the filter cake with water, and dry in vacuum to obtain 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde.

Embodiment 3

[0026] Add 300ml of tetrahydrofuran (THF), 12.0g of Mg powder, 5g of trans-1,4-dichloro-2-butene (content: 99.0%), and 0.1g of iodine in a 1000ml flask, heat to initiate, and then control the reaction The temperature is 30-35°C, add the remaining 26.6g of trans-1,4-dichloro-2-butene dropwise, after the drop is complete, raise the temperature to 50°C, keep warm until the Mg powder disappears completely; Add dropwise 200ml of THF solution containing 118g of dimethoxyacetone. After dropping, keep the temperature for 8 hours and cool down to 20°C; dropwise add the reaction solution into 300ml of 10% dilute sulfuric acid for hydrolysis, control the hydrolysis temperature below 20°C, drop Continue to stir for 30 minutes after completion, and a large amount of product precipitates out; the temperature is controlled below 50°C, THF is removed under reduced pressure, 300ml of water is added thereto, filtered, the filter cake is rinsed with a small amount of water, and the wet product is...

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Abstract

The invention discloses a new method for synthesis of 2, 7-dimethyl-2, 4, 6-octatrien-1, 8-dialdehyde. The method synthesizes 2, 7-dimethyl-2, 4, 6-octatrien-1, 8-dialdehyde using trans-1, 4-dichloro-2-butylene as the raw material, which undergoes Grignard reaction, condensation reaction and acidic hydrolysis reaction. The method has the advantages that, firstly, trans-1, 4-dichloro-2-butylene is adopted as the raw material for synthesizing 2, 7-dimethyl-2, 4, 6-octatrien-1, 8-dialdehyde after three procedural reactions, so the total yield is high; secondly, synthesis of 2, 7-dimethyl-2, 4, 6-octatrien-1, 8-dialdehyde has good reaction selectivity and little by-products; and thirdly, the process is simple with convenient operation.

Description

technical field [0001] The invention relates to a synthesis method of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde. Background technique [0002] 2,7-Dimethyl-2,4,6-octatriene-1,8-dialdehyde, melting point 157-159°C, stable at room temperature, easily soluble in ethanol, petroleum ether, slightly soluble in water, is a synthetic The key intermediate of carotenoids has important applications in the synthesis of β-carotene, canthaxanthin and astaxanthin, and its synthesis has not been reported in domestic literature. Carotenoids can be used as drugs, pigments, food additives and feed additives in medicine, food, cosmetics and aquaculture. With the increasing application of carotenoids in our country, the research on the synthesis of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde is of great significance. Bibliographical reports 2,7-dimethyl-2,4,6-octatriene-1, the synthetic method of 8-dialdehyde mainly contains following several kinds: [0003] 1. In 1959, Isler of Roche Com...

Claims

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Application Information

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IPC IPC(8): C07C47/21C07C45/00
Inventor 李浩然黄国东陈志荣王正江周贵阳曾庆宇黄高峰
Owner ZHEJIANG UNIV
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