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Modified synthetic method of methyl nonyl acetaldehyde intermediate

A synthesis method and technology of methyl nonyl ketone, applied in the field of chemistry, can solve problems such as reducing the rate of alkylation reaction

Inactive Publication Date: 2016-08-10
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The existing method uses methanol or ethanol as a solvent in the first step of the reaction, but because the alcohol reagent is combined with the cation and is also combined with the enolate anion through hydrogen bonds, the existence of hydrogen bonds reduces the amount of alkyl in the condensation process. speed of reaction

Method used

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  • Modified synthetic method of methyl nonyl acetaldehyde intermediate
  • Modified synthetic method of methyl nonyl acetaldehyde intermediate
  • Modified synthetic method of methyl nonyl acetaldehyde intermediate

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Embodiment 2

[0015] Dissolve 7.6 g (0.14 mol) of sodium methoxide in 40 ml of cyclohexane, cool down to 5 °C under stirring, slowly add 17.3 g (0.1 mol) of methyl nonyl ketone (I) and 13.2 g of methyl chloroacetate (0.12 mol) the mixed solution of (II), the dropwise addition process is about 40 minutes, continue to keep warm for 5 hours (within the range of 4.5 to 5.5 hours), after the reaction is complete, add dilute hydrochloric acid to the reaction solution to terminate the reaction, adjust the pH The value is 4. After filtering to remove solid impurities, the organic layer is distilled under reduced pressure to recover cyclohexane and methyl nonyl ketone (I), which are separated by thin-layer chromatography and dichloromethane:petroleum ether=10:1 The lotion was rinsed and separated by silica gel column chromatography to obtain 3-methylepoxydodecanoic acid methyl ester (III), and the reaction yield reached 89.6%.

Embodiment 3

[0017] Dissolve 7.0 g (0.13 mol) of sodium methoxide in 40 ml of cyclohexane, cool down to 5 °C under stirring, slowly add 17.3 g (0.1 mol) of methyl nonyl ketone (I) and 13.2 g of methyl chloroacetate (0.12 mol) the mixed solution of (II), the dropwise addition process is about 40 minutes, continue to keep warm for 5 hours (within the range of 4.5 to 5.5 hours), after the reaction is complete, add dilute hydrochloric acid to the reaction solution to terminate the reaction, adjust the pH The value is 4. After filtering to remove solid impurities, the organic layer is distilled under reduced pressure to recover cyclohexane and methyl nonyl ketone (I), which are separated by thin-layer chromatography and dichloromethane:petroleum ether=10:1 The lotion was rinsed and separated by silica gel column chromatography to obtain 3-methylepoxydodecanoic acid methyl ester (III), and the reaction yield reached 87.9%.

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Abstract

The invention introduces a novel synthetic method of intermediate 3-methyl epoxy methyl dodecanoate of aldehyde flavour methyl nonyl acetaldehyde. The method includes performing reaction of methyl chloroacetate and methyl nonyl ketone to form 3-methyl epoxy methyl dodecanoate, using sodium ethoxide as a catalyst, using nonpolar cyclohexane as a solvent which is beneficial to react to the direction of generating product, and processing by routine method after the reaction to prepare the required compound. The technology is stable, and has simple operation and good reproducibility. The used raw materials are simple and easily available, the cyclohexane solvent is easy to recycle, and the product has high yield and good quality.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a preparation method of 3-methylepoxymethyl dodecanoate, an aldehyde fragrance intermediate. Background technique [0002] Methyl nonacetaldehyde is an important raw material used to prepare modern flavors. Its molecular formula is, and its chemical structural formula is: [0003] [0004] Methyl nonacetaldehyde has an aldehyde aroma accompanied by ambergris and other notes. It has the characteristics of strong aroma, good diffusion and long-lasting fragrance. It is often used in the preparation of aldehyde aroma notes. At present, the synthesis method of methyl nonyl aldehyde is a three-step reaction: 1. taking methyl nonyl ketone (I) and methyl chloroacetate (II) as raw materials to obtain 3-methyl epoxydodecanoic acid methyl ester through Darzens condensation ( III); 2. 3-methylepoxydodecanoic acid methyl ester is hydrolyzed and saponified to obtain 3-methylepoxydodeca...

Claims

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Application Information

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IPC IPC(8): C07D301/02C07D303/48
CPCC07D301/02C07D303/48
Inventor 何磊周敏冯良东
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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