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US 2014/0005442 A1Published application
Intermediate of lycopene and preparation method of intermediate
AssigneesShaoxing University, Zhejiang Medicine Co., Ltd. Xinchang
InventorsRunpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Abstract
The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.
Claims17
A method of preparing 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde of formula (3), comprising the following three steps:
- Step I:
- 3-methyl-4,4-dialkoxy-1-aldehyde of formula (11) undergoing a Wittig-Horner condensation reaction with tetra-alkyl methylene diphosphonate at temperature of 0˜30° C. in ether solvent or dipolar aprotic solvent and under protection of inert gas in the presence of bases, to produce 4-methyl-5,5-dialkoxy -1-pentenyl-1-phosphoric acid dialkyl ester of formula (10);
- the reaction sequence is described as follows:
- Step II comprises Step II-1 and Step II-2, wherein,
- Step II-1:
- 4-methyl-5,5-dialkoxy-1-pentenyl-1-phosphoric acid dialkyl ester of formula (10) undergoing a rearrangement reaction at temperature of −40˜30° C. in ether solvent or dipolar aprotic solvent and under protection of inert gas in the presence of bases;
- Step II-2:
- adding 6-methyl-5-heptene-2-one of formula (13) to the product of Step II-1 to undergo a Wittig-Horner condensation reaction at temperature of −40˜30° C. in ether solvent or dipolar aprotic solvent and in the presence of bases to produce 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecan-triene of formula (12);
- the reaction sequence is described as follows:
- Step III:
- mixing2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecan-triene of formula (12) with acid catalysts, water and homogeneous solvents to undergo a hydrolysis reaction at the temperature of 10˜35 under protection of inert gas to produce 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde of formula (3);
- the reaction sequence of Step III is described as follows:
9 more elements
Dependencies are inferred from the claim text.