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Asymmetric synthesis method of dextral citronellal

An asymmetric, citronellal technology, applied in the field of asymmetric synthesis of organic chemistry, can solve the problems of difficult reuse of trans-citral, high production equipment requirements, etc., and achieve the effects of simple catalyst preparation, mild reaction conditions, and convenient recovery.

Inactive Publication Date: 2014-04-16
GUANGDONG FOOD IND INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The synthesis process of this synthetic route is simple, but the rectification of the cis-trans isomer mixture of citral to obtain the cis configuration requires high production equipment, and the obtained trans-citral is difficult to reuse

Method used

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  • Asymmetric synthesis method of dextral citronellal
  • Asymmetric synthesis method of dextral citronellal
  • Asymmetric synthesis method of dextral citronellal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Take a 250ml three-necked flask, and add citral (15.2g, 0.1mol), (R)-2-[bis(phenyl)]methyltetrahydropyrrole (24mg, 0.1mmol) to it successively under nitrogen protection, Trifluoroacetic acid (12 mg, 0.1 mmol), 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate diethyl ester (75.9 g, 0.3 mol), and 80 ml of benzene was added to dissolve the solid . Stir at room temperature for 10 h, remove the solvent under reduced pressure, and purify by column chromatography to obtain 13.9 g of (R)-citronellal light yellow liquid with a yield of 90% and an ee value of 80%.

Embodiment 2

[0033] Take a 250ml three-necked flask, add citral (15.2g, 0.1mol) and (R)-2-[bis(4-methylphenyl)]methyltetrahydropyrrole (27mg, 0.1mmol), trichloroacetic acid (16mg, 0.1mmol), 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate diethyl ester (75.9g, 0.3mol), and add 80ml THF dissolved the solid. Stir at -20°C for 20 h, remove the solvent under reduced pressure, and purify by column chromatography to obtain 13.5 g of (R)-citronellal light yellow liquid with a yield of 88% and an ee value of 80%.

Embodiment 3

[0035] Take a 250ml three-necked flask, add citral (15.2g, 0.1mol), (R)-2-[bis(4-tert-butylphenyl)]methyltetrahydropyrrole (35mg , 0.1mmol), trifluoroacetic acid (12mg, 0.1mmol), 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate diethyl ester (25.3g, 0.1mol), and Add 80 mL of tetrahydrofuran to dissolve the solid. Stir at 30°C for 24 h, remove the solvent under reduced pressure, and purify by column chromatography to obtain 13.6 g of (R)-citronellal light yellow liquid with a yield of 88% and an ee value of 82%.

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Abstract

The invention discloses an asymmetric synthesis method of dextral citronellal. The method takes citral as a starting material, dihydropyridine derivative as a negative hydrogen source, and chiral amine salt as a chiral auxiliary agent, and asymmetric hydrogenation reaction is generated in a bi-catalytic system to synthesize dextral citronellal. By adopting the synthesis method disclosed by the invention for the synthesis of dextral citronellal, the total yield is more than 85%, and the ee (enantiomeric excess) value is greater than 80%; the synthesis method has the characteristics of mild reaction conditions, simple synthesis process, simple catalyst preparation, convenience in recycling and the like, and is suitable for industrial production of dextral citronellal.

Description

technical field [0001] The invention belongs to the technical field of asymmetric synthesis of organic chemistry, and specifically relates to a method for asymmetrically synthesizing D-citronellal by using citral as a starting material. Background technique [0002] Citronellal (3,7-dimethyl-6-octenal) has 1 chiral center and has 2 stereoisomers. It has lemon, lily, rose fragrance. It is widely used in food flavors to prepare citrus and cherry flavors, and is also used to prepare low-grade soap flavors. It is a raw material for other flavors. For example, hydrogenated citronellal can produce citronellol, and (S)-citronellol has a very fresh rose petal scent, while (R)-citronellol has a light oily scent with a pungent rose petal scent. [0003] Generally speaking, citronellal is an important intermediate for obtaining different acyclic terpenoid aroma compounds, such as citronellyl ester, citronellonitrile, dihydrocitronellal, dihydrocitronellol, etc. Moreover, citronellal...

Claims

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Application Information

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IPC IPC(8): C07C47/21C07C45/62
CPCY02P20/584C07C45/62C07C47/21
Inventor 王三永李春荣蓝温龙杨定乔曾伟山
Owner GUANGDONG FOOD IND INST
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