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New synthesis process of 1,1,8,8-tetramethoxy-2,7-dimethyl-2,4,6-octatriene

A tetramethoxy, dimethyl technology, applied in the field of organic synthesis, can solve the problems of high cost, high cost, low yield and the like, and achieve the effect of improving yield

Inactive Publication Date: 2009-12-09
GUANGZHOU WISDOM BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Due to the low yield and high cost of synthesizing this intermediate with 1,4-tetraethyl diphosphate-2-butene and acetonaldehyde dimethyl acetal as starting materials, Yang Zehui, Yan Haiying, Li Maolin, Xu Wei, Wang Jiarong, Chen Xinzhi; "Study on a new synthesis process of 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde"; Journal of Zhejiang University (Natural Science Edition); Volume 32, Issue 6, November 2005 Another route was used to synthesize 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde instead of this intermediate, but the starting material 4-acetoxy Base-2-methyl-2-butenal is a key intermediate for the synthesis of vitamin A acetate, and it is also very expensive, and the market does not buy this intermediate. US 4916250 reports using aceglyoxal dimethyl acetal and 1,4- Tetraethyl diphosphate-2-butene is used as a raw material to synthesize this intermediate, but the yield is only 62%. US 5107030 has made many improvements on the basis of US 4916250, but the highest yield can only be 79%. Calculated with the price of carotene and carotenoid products, the yield cannot meet the requirements of industrialization

Method used

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  • New synthesis process of 1,1,8,8-tetramethoxy-2,7-dimethyl-2,4,6-octatriene

Examples

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Effect test

example 1

[0023] Take 32.8 grams (0.1 mole) of 1,4-diphosphate tetraethyl-2-butene and 23.6 grams (0.2 mole) of pyruvaldehyde dimethyl acetal into the reactor, add 1 liter of toluene and 1 liter of Cyclohexane, then add 32.8 grams of potassium carbonate, and finally add 30 grams of basic alumina with 12 grams of sodium hydroxide and 0.01 grams of 18-crown-6. Stir at room temperature for 4 hours. After the reaction is over Wash with 1 liter of water, divide the organic layer, dry with anhydrous sodium sulfate, filter, evaporate the solvent, and then evaporate the residual solvent and unreacted raw materials under a high vacuum of 0.20mmHg. The final 232 grams of product is analyzed by proton NMR Purity, the yield is 90%.

example 2

[0025] Take 32.8 g (0.1 mole) of 1,4-diphosphate tetraethyl-2-butene and 23.6 g (0.2 mole) of pyruvaldehyde dimethyl acetal into the reactor, add 1.25 liters of toluene and 1.25 liters of Cyclohexane, then add 16.4 grams of potassium carbonate, and finally add 30 grams of basic alumina with 14 grams of sodium hydroxide and 0.02 grams of 18-crown-6. Stir at room temperature for 4 hours. The post-treatment is the same. In Example 1, 230 grams of product were obtained, and the yield was 89%.

example 3

[0027] Take 32.8 grams (0.1 mole) of 1,4-diphosphate tetraethyl-2-butene and 23.6 grams (0.2 mole) of pyruvaldehyde dimethyl acetal into the reactor, add 1 liter of toluene and 1 liter of Cyclohexane, then add 16.4 grams of sodium sulfate, and finally add 30 grams of basic alumina with 16.8 grams of potassium hydroxide and 0.02 grams of 12-crown-4. Stir at room temperature for 4 hours. The post-treatment is the same. In Example 1, 210 grams of product were obtained, and the yield was 81.5%.

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Abstract

The invention discloses a new synthesis process of 1,1,8,8-tetramethoxy-2,7-dimethyl-2,4,6-octatriene. The original process is improved; wherein, alkali metal hydroxide or alkali metal alkylate is fixed on the carrier which is added into the reaction system and crown ether of 18-crown-6 or 12-crown-4 is added as catalyst, thus obviously improving the yield of 1,1,8,8-tetramethoxy-2,7-dimethyl-2,4,6-octatriene.

Description

Technical field [0001] The invention relates to the field of organic synthesis, in particular to a new process for synthesizing 1,1,8,8-tetramethoxy-2,7-dimethyl-2,4,6-octatriene. Background technique [0002] 1,1,8,8-Tetramethoxy-2,7-dimethyl-2,4,6-octatriene is a key intermediate for the synthesis of carotenoids and carotenoids. Its structure is shown in the figure Shown: [0003] [0004] Since 1,4-diphosphate tetraethyl-2-butene and pyruvaldehyde dimethylacetal are used as starting materials to synthesize this intermediate with low yield and high cost, Yang Zehui, Yan Haiying, Li Maolin, Xu Wei, Wang Jiarong, Chen Xinzhi; "Study on the New Synthesis Process of 2,7-Dimethyl-2,4,6-octatriene-1,8-dialdehyde"; Journal of Zhejiang University (Science Edition); Volume 32, Issue 6, 2005 11 Use another route to synthesize 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde without going through this intermediate, but the starting material 4-acetoxy 2-methyl-2-butenal is a key intermediate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/303C07C41/48B01J31/02
Inventor 吴世林邸维龙
Owner GUANGZHOU WISDOM BIO TECH
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