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Preparation method of 2,7-dimethyl-2,4,6-octatriene-1,8-dial

A technology of octatriene and dimethyl, which is applied in the field of preparation of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde, which can solve the problem of long reaction route and high three wastes , poor selectivity and other problems, to achieve the effect of easy industrial production and simple process

Active Publication Date: 2018-11-06
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] In summary, it can be seen that the current method for preparing 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde has difficulties in purchasing raw materials, low reaction yield, poor selectivity, and long reaction route , the three wastes are relatively difficult, so it is necessary to find a new synthesis method of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde to solve the above technical problems

Method used

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  • Preparation method of 2,7-dimethyl-2,4,6-octatriene-1,8-dial

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Embodiment 1

[0039] The preparation of embodiment 1 compound V

[0040] Weigh 100g of tetrahydrofuran and 24g (1mol) of magnesium flakes in a 2L three-necked flask, then add 0.1g of iodine to initiate the reaction, then add dropwise 106.5g (0.5mol) of 1,4-dibromo-2-butene and 500g of For the mixed solution of tetrahydrofuran, control the internal temperature of the reaction at 55-60 ° C, drop it completely in about 2 hours, continue the insulation reaction for 1 hour after the drop is complete, and then add 44.1 g of ethylene oxide dropwise to the reaction solution, and control the reaction temperature not to exceed 60 ℃, 2h dropwise addition is complete, after the dropwise addition is complete, continue the insulation reaction for 2h, slowly pour the reaction solution into 300g 5wt% hydrochloric acid for acidolysis, the acidolysis temperature does not exceed 10°C, continue to stir for 30min after the addition is complete, and separate the liquid. Tetrahydrofuran was removed under reduced ...

Embodiment 2

[0041] The preparation of embodiment 2 compound V

[0042] Weigh 100g of tetrahydrofuran and 25.2g (1.05mol) of magnesium flakes in a 2L three-necked flask, then add 0.1g of iodine to initiate the reaction, and then dropwise add 106.5g (0.5mol) of 1,4-dibromo-2-butene into the system Mixed solution with 500g tetrahydrofuran, control the internal temperature of the reaction at 55-60°C, and drop it completely in about 3 hours. When the temperature exceeds 60°C, the dropwise addition is complete in about 3 hours. After the dropwise addition is complete, continue to keep warm for 1 hour. Slowly pour the reaction solution into 300g of 5% hydrochloric acid for acidolysis. The acidolysis temperature does not exceed 10°C. After the addition is complete, continue to stir for 30 minutes. Liquid separation, removal of THF under reduced pressure (absolute pressure 1000Pa, temperature 45°C), and then vacuum oil pump drying (vacuum absolute pressure 30Pa, drying temperature 50°C), to obtain...

Embodiment 3

[0043] The preparation of embodiment 3 compound VI

[0044] Weigh 28.8g (0.2mol) of compound V prepared in Example 1, 200g of dichloromethane, 0.3g (0.002mol) of 2,2,6,6-tetramethylpiperidine oxide in a 500ml three-necked flask, at 20°C Under stirring, oxygen gas is blown into the system at a speed of 100ml / min. The reaction process is detected by gas phase, and the reaction of compound V is complete in about 5h. In the system, 100g of water is added to terminate the reaction, liquid separation, and the organic phase solvent (absolute Pressure 1000Pa, temperature 30°C), and then vacuum oil pump drying (vacuum absolute pressure 20Pa, drying temperature 50°C), to obtain 25.6g of compound VI, product gas phase purity 99.5%, yield 91.4%.

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Abstract

The invention discloses a preparation method of 2,7-dimethyl-2,4,6-octatriene-1,8-dial. The preparation method comprises the following steps: a) reacting 1,4-dibromo-2-buten as shown in a formula II with magnesium to obtain a Grignard reagent as shown in a formula III; b) reacting the Grignard reagent as shown in the formula III with ethylene oxide as shown in a formula IV, and performing acidolysis to obtain a compound V; c) performing an oxidation reaction on the compound V to obtain a compound VI; d) performing an aldol condensation reaction on the compound VI and formaldehyde to obtain a compound VII; and e) performing a hydroisomerization reaction on the compound VII to obtain 2,7-dimethyl-2,4,6-octatriene-1,8-dial as shown in a formula I, wherein the reaction equation is shown in thedescription. The preparation method has the advantages that the raw materials are easy to get, the reaction yield is high, the process is simple, and the industrial production is facilitated.

Description

technical field [0001] The invention relates to a preparation method of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde, which belongs to the field of organic synthesis. Background technique [0002] 2,7-Dimethyl-2,4,6-octatriene-1,8-dialdehyde, referred to as "decenal", the molecular formula is C 10 h 12 o 2 , molecular weight 164.2, CAS: 5056-17-7, dedecenal is usually light yellow powdery solid, melting point 157.0-159.0°C, easily soluble in methanol, dichloromethane, soluble in petroleum ether, ethyl acetate, slight Soluble in water, it is a key intermediate in the synthesis of carotenoids, and has important applications in the synthesis of β-carotene, canthaxanthin, astaxanthin, and lycopene. [0003] The synthesis methods of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde reported in the literature mainly include the following: [0004] [0005] The above route is the process route reported by patents US20020128520, US6673972, US5300658, US5382732, etc., with furan as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/67C07C47/21
CPCC07C29/106C07C45/38C07C45/67C07C45/75C07F3/02C07C47/21C07C33/035
Inventor 刘英瑞张涛吕英东郭劲资张旭程晓波王延斌朱龙龙林龙李莉宋军伟陈志刚王展黎源
Owner WANHUA CHEM GRP CO LTD
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