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Synthesis method of geosmin

A synthetic method, the technology of geosmin, which is applied in the direction of organic chemistry, oxygen-containing functional group reduction preparation, etc., can solve the problems of risk, high cost, difficulty in obtaining raw materials, etc., to ensure product purity and yield, and reduce preparation Effect of less cost and solvent usage

Inactive Publication Date: 2012-07-11
天津市佰斯康科技有限公司 +1
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Problems solved by technology

In 1968, Marshall and Hochstetler reported the synthetic method of geosmin (J.Org.Chem., 1968, 2593) using methyl octahydronaphthalene as raw material, because the methyl octahydronaphthalene used in this method is relatively expensive and not easy to obtain , so not suitable for mass production
Ayer et al reported the use of methylcyclohexanone and 1-chloro-3-pentanone in 1976 as a method for the synthesis of geosmin as a raw material (Can.J.Chem., 1976,3276), due to the 1 used in the method -Chloro-3-pentanone raw materials are relatively expensive, and a large amount of dangerous Raney nickel catalysts need to be used in the synthesis process, so this method is not suitable for mass production
In 1993, Boland et al. reported the method (Helv.Chim.Acta, 1993, 1949) of using 4-methanolyl-tetralin as raw material to prepare geosmin, because the raw material is difficult to obtain, and it needs to use expensive Enzyme catalyst, making this method can not be applied in actual production
In the synthetic method reported by Groot et al. in 1992 (Tetrahedron, 1992, 5497), relatively dangerous ozonation and lithium tri-sec-butyl borohydride are used, and the synthetic route is relatively complicated, so it is not easy to carry out mass production
Revial ​​reported in 1989 the method (Tetrahedron Lett., 1989, 4121) using methylcyclohexanone as a raw material to prepare geosmin, but this document did not provide detailed and precise experimental details, so it could not be repeated
In a word, because the above-mentioned synthetic methods have defects, resulting in high risk and high cost, they are only suitable for small-scale milligram-level preparation, and cannot be mass-produced on a large scale. Therefore, the current mass production of high-purity geosmin Has become the bottleneck of related industries

Method used

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  • Synthesis method of geosmin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1) Add 9 grams of 2-methylcyclohexanone into a four-necked flask, then add 40 grams of toluene and 13 grams of (S)-α-phenylethylamine in turn at room temperature. After the addition is complete, the above reaction solution Heat to reflux and stir for 6 hours, stop stirring, distill the toluene to obtain the crude product, and distill the crude product under reduced pressure to obtain 13 g of intermediate 1, yield: 75%.

[0029] 2) Mix 13 g of intermediate 1 and 5.3 g of pentenone at room temperature, then stir the above reaction solution at room temperature for 24 hours, stop stirring to obtain 18.3 g of intermediate 2, yield: 100%.

[0030] 3) Mix 18.3 grams of intermediate 2 with 4 grams of glacial acetic acid at room temperature, then stir the above reaction solution at room temperature for 1 hour, add 30 grams of ethyl acetate for dilution, and wash the resulting solution with saturated sodium bicarbonate solution and water until The aqueous phase was neutral, and t...

Embodiment 2

[0037] 1) Add 13.5 grams of 2-methylcyclohexanone into a four-necked flask, then add 55 grams of toluene and 16.2 grams of (S)-α-phenylethylamine in turn at room temperature, and after the addition is complete, the above reaction solution Heat to reflux and stir for 10 hours, stop the stirring, distill off the toluene to obtain a crude product, which is distilled under reduced pressure to obtain 20.5 g of intermediate 1, yield: 79%.

[0038] 2) 20.5 g of intermediate 1 and 8.8 g of pentenone were mixed at room temperature. After the mixing, the above reaction solution was stirred at room temperature for 30 hours, and the stirring was stopped to obtain 29.3 g of intermediate 2. The yield: 100%.

[0039] 3) Mix 29.3 grams of intermediate 2 with 9 grams of glacial acetic acid at room temperature, stir the above reaction solution at room temperature for 3 hours, add 40 grams of ethyl acetate to dilute, and wash the resulting solution with saturated sodium bicarbonate solution and w...

Embodiment 3

[0046] 1) Add 18.9 grams of 2-methylcyclohexanone into a four-necked flask, then add 90 grams of toluene and 41 grams of (S)-α-phenylethylamine in turn at room temperature, and after the addition is complete, the above reaction solution Heat to reflux and stir for 10 hours, stop stirring, distill off the toluene to obtain a crude product, which is distilled under reduced pressure to obtain 29.4 g of intermediate 1, yield: 81%.

[0047] 2) 29.4 g of intermediate 1 and 14.7 g of pentenone were mixed at room temperature. After the mixing was completed, the above reaction solution was stirred at room temperature for 48 hours, and the stirring was stopped to obtain 44.1 g of intermediate 2, yield: 100%.

[0048] 3) Mix 44.1 grams of intermediate 2 with 9 grams of glacial acetic acid at room temperature, stir the above reaction solution at room temperature for 5 hours, add 15 grams of ethyl acetate to dilute, and wash the resulting solution with saturated sodium bicarbonate solution ...

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Abstract

The invention provides a synthesis method of geosmin. The method is characterized in that 2-methyl cyclohexanone used as a raw material for an initial reaction firstly is in ammoniation reaction with (S)-Alpha-phenylethylamine to produce an enimic compound; the enimic compound is in substitution reactio with olefine ketone to produce an enimic compound substituted by pentyl ketone; afterwards, the enimic compound is converted to a cyclohexanone derivative under an acidic condition; Alpha, Beta unsaturated derivatives are produced through intramolecular cyclization under an alkaline condition; and the enimic compound is subject to reactions of epoxidation reaction, reduction, dehydroxylation, and the like to produce the final target compound, namely the geosmin. The synthesis method of the geosmin, which is provided by the invention, has the advantages that the efficiency is high, the operation is simple, convenient and safe, the costs of raw materials used for the reactions are low, the use amount of solvents is small, and the preparation cost can be reduced on the premise that the product purity and the yield are guaranteed, so that the synthesis method is very suitable for hundred-milligram scale batch production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fine chemicals, and in particular relates to a synthesis method of geosmin suitable for batch production of hundreds of milligrams. Background technique [0002] Geosmin, also known as geosmin and geosmin, is a compound with a strong earthy smell. It is synthesized by actinomycetes and cyanobacteria and secreted into water. It is absorbed by aquatic animals and produces peculiar smell. It is a compound of certain algae. One of two metabolites (geosmin and dimethylisoborneol) produced by blooms. Gerber and Lechevalier reported a method for isolating geosmin from soil in 1965 (Appl. Microbiol., 1965, 935). In 1968, Marshall and Hochstetler reported the synthetic method of geosmin (J.Org.Chem., 1968, 2593) using methyl octahydronaphthalene as raw material, because the methyl octahydronaphthalene used in this method is relatively expensive and not easy to obtain , so it is not suitable for mass...

Claims

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Application Information

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IPC IPC(8): C07C35/36C07C29/132
Inventor 袁家龙符新亮陈晓邱永宽马康苏福海何雅娟
Owner 天津市佰斯康科技有限公司
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