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Preparation method of 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde

A trimethyl, 10-technology, applied in the field of synthesis of lycopene intermediates, can solve the problems of difficult synthesis, difficult industrial production, and difficult sources, and achieve the effects of low cost, easy raw materials, and simple process routes

Inactive Publication Date: 2013-02-13
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has more industrialization potential, the source of the raw material 4-methyl-5,5-dialkoxy-1-pentene-1-phosphonic acid dialkyl ester used is difficult, and the synthesis is also difficult. Difficult to apply to industrial production

Method used

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  • Preparation method of 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde
  • Preparation method of 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde
  • Preparation method of 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Example 1: Preparation of 2,6,10-trimethyl-2,5,9-undecatrien-1-al (Formula 2).

[0026] Add 15 grams of L-proline (0.13mol) and 50 milliliters of water into a 500-mL four-neck flask, stir mechanically at 45°C, add dropwise 116 grams of propionaldehyde (2.0 mol), 166 grams of 4,8-dimethyl The mixture of 3,7-nonadien-1-al (6) (1.0mol) and 150 ml of toluene was added dropwise in about 30 minutes, and after stirring for 10 minutes, the reaction solution was cooled to room temperature and left to stand. The layers were separated, the water layer was extracted with 20 ml of toluene (the water layer was the catalyst layer and could be recycled), the combined organic layers were washed with saturated brine, dried, the solvent was recovered, and the target product 2 with a GC content of 96.1% was obtained by rectification under reduced pressure. 170.6 g of 6,10-trimethyl-2,5,9-undecatrien-1-al, yield 79.6%.

[0027] Product structure confirmation:

[0028] 1 HNMR (δppm, 400MH...

Embodiment 2

[0033] Example 2: Preparation of 2,6,10-trimethyl-2,5,9-undecatrien-1-al (Formula 2).

[0034] Add 30g of acetic acid (0.5mol) and 30ml of water into a 500mL four-neck flask, slowly add 56g of 40% dimethylamine aqueous solution (0.5mol), and add 87g of propionaldehyde dropwise at 65°C under mechanical stirring (2.5mol), 166 grams of 4,8-dimethyl-3,7-nonadien-1-al (6) (1.0mol) and 150 ml of dichloroethane, the mixture was added dropwise in about 30 minutes , continue stirring and reacting for 10 minutes, cool the cooled reaction solution to room temperature and let stand to separate layers. The water layer is extracted with 20 ml of dichloroethane (the water layer is the catalyst layer, which can be recovered and used mechanically). The combined organic layers are washed with saturated brine and dried. , recovered the solvent, and rectified under reduced pressure to obtain 178.2 g of the target product 2,6,10-trimethyl-2,5,9-undecatrien-1-al with a GC content of 97.4%, with a y...

Embodiment 3

[0036] Example 3: Preparation of 2,6,10-trimethyl-2,5,9-undecatrien-1-al (2).

[0037]Add 40 grams of acetic acid (0.25mol) and 20 milliliters of water into a 500-mL four-neck flask, slowly add 28 grams of 40% dimethylamine aqueous solution (0.25 mol), and add 145 grams of propionaldehyde dropwise at 80°C under mechanical stirring (2.5mol), 166 grams of 4,8-dimethyl-3,7-nonadien-1-al (6) (1.0mol) and 150 ml of isobutyl acetate, the mixture was added dropwise in about 30 minutes , continue to stir and react for 10 minutes, cool the reaction solution to room temperature and let stand to separate layers, extract the water layer with 20 ml of isobutyl acetate (the water layer is the catalyst layer, which can be recycled and applied), the combined organic layers are washed with saturated brine, and dried , recovered the solvent, and rectified under reduced pressure to obtain 172.2 g of the target product 2,6,10-trimethyl-2,5,9-undecatrien-1-al with a GC content of 96.4%, with a yie...

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Abstract

The invention discloses a preparation method of 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and relates to the technical field of synthesis of a lycopene intermediate. The preparation method is characterized by comprising the following steps of using 4,8-dimethyl-3,7-violetleaf-1-aldehyde and propionaldehyde to serve as raw materials, and conducting a one-step condensation reaction to generate the key lycopene intermediate 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde. The preparation method is simple and rapid in process route, prone to obtain the raw materials and low in cost and has industrial value. In particular, a catalytic agent can be simply layered to recover and use indiscriminately after the reaction is finished.

Description

Technical field: [0001] The invention relates to the synthesis of lycopene intermediates, in particular to a preparation method of 2,6,10-trimethyl-2,5,9-undecanetrien-1-aldehyde. Background technique: [0002] There are about 600 carotenoids in nature, but only six of them can be used in industrial production. The manufacturers are Roche and BASF. As one of the important products, lycopene plays an important role in scavenging free radicals, anti-aging, inhibiting tumors, and treating heart disease. It is widely used in drugs, food additives, and feed additives. Roche company has developed a synthetic route characterized by the Wittig reaction, in which the expensive and toxic raw material triphenylphosphine is used; other early synthetic methods also use triphenylphosphine. Since Babler pioneered the route characterized by C15 phosphonate, Shen Runpu and others have successively applied for a total synthesis route of lycopene characterized by Wittig-Horner condensation re...

Claims

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Application Information

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IPC IPC(8): C07C45/74C07C47/21
Inventor 沈润溥吴春雷吴永华吴毅斌鲁瑞娟王林霞
Owner SHAOXING UNIVERSITY
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