Synthesis method of ionone-type spice intermediate products

A technology for the synthesis of ionones and synthetic methods, which is applied in the synthesis of ionone-based fragrance intermediates and the field of compound synthesis, which can solve the problems of low space-time yields and high catalyst costs, and achieve fewer reaction steps, high yields, and less pollution. Effect

Active Publication Date: 2015-03-18
ANHUI BBCA FERMENTATION TECH ENG RES
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the disadvantage of very low space-time yield and high catalyst cost

Method used

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  • Synthesis method of ionone-type spice intermediate products
  • Synthesis method of ionone-type spice intermediate products
  • Synthesis method of ionone-type spice intermediate products

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Put 100g (98.5% content) dehydrolinalool, 91.0g methyl acetoacetate and 4.0g aluminum isopropoxide into a 500ml pressure-resistant reaction flask, magnetically stir and heat to an internal temperature of 85°C with an oil bath to keep the reaction The pressure was 1.2 MPa to react for 2 hours, and the conversion rate of dehydrolinalool was 98.8% analyzed by gas chromatography. After the reaction is completed, fill with nitrogen to normal pressure, cool down to 15°C, add 50 ml of 0.5% sodium hydroxide methanol solution dropwise, and keep the temperature for 1.5 hours after dropping. After the isomerization is completed, add acetic acid to adjust the pH value between 6 and 7. The reaction solution was filtered on a column equipped with diatomaceous earth filter aid using methanol as a solvent, and the filtrate was rectified to obtain 97.5% (sum of cis-trans) pseudoionone product 117.3g. The yield of pseudoionone is about 93.1%

Embodiment 2

[0035] According to the method of Example 1, the only difference is that in this example, 91.0 g of methyl acetoacetate was changed to 83.5 g of methyl acetoacetate, and other conditions remained unchanged. The conversion rate of dehydrolinalool was 97.6%, and 114.5 g of pseudoionone product with a content of 98.1% was obtained. The yield of pseudoionone is about 92.5%

Embodiment 3

[0037] According to the method of Example 1, the only difference is that in this example, 91.0 g of methyl acetoacetate was changed to 98.5 g of methyl acetoacetate, and other conditions remained unchanged. The conversion rate of dehydrolinalool was 99.2%, and 114.3 g of pseudoionone product with a content of 97.8% was obtained. The yield of pseudoionone is about 92.1%.

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Abstract

The invention discloses a synthesis method of ionone-type spice intermediate products, namely pseudoionone and methyl pseudoionone, wherein the pseudoionone and the methyl pseudoionone are prepared by taking dehydrogenated linalool as a raw material, reacting with a compound represented as the formula I under an appropriate catalyst condition, and implementing an isomerization reaction. The method disclosed by the invention, in preparing the ionone-type spice intermediate products, is few in reaction steps, high in yield and low in pollution, wherein the R1 represents either -H or -CH3; and R2 represents methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, 2-methyl propyl, n-amyl, isoamyl, 2-methyl butyl, benzyl or other groups.

Description

Technical field [0001] The invention relates to a method for synthesizing a compound, belonging to the field of organic synthesis, and in particular to a method for synthesizing an ionone-based perfume intermediate. Background technique [0002] Pseudoionone and methyl pseudoionone are important intermediates for synthesizing ionone, which are widely used in perfume, medicine, and food additive industries. Ionone is a precious spice with woody aroma. It is one of the largest and most important spices in the perfume industry. The synthesized β-ionone is an important intermediate for the synthesis of vitamin A and β-carotene. [0003] For a long time, domestic and foreign scholars have been continuously conducting research on the improvement of the synthesis process of pseudoionone and its homologues. The main synthesis method is prepared by Aldol condensation of citral with acetone under alkaline conditions, and citral is mainly obtained by rectifying and purifying Litsea cubeba oi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/203C07C45/67
Inventor 李荣杰尚海涛杨为华邓远德张飞
Owner ANHUI BBCA FERMENTATION TECH ENG RES
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