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Synthesis method of ionone-type spice intermediate products

An ionone and a synthesis method technology are used in the synthesis of ionone-based fragrance intermediates and the field of compound synthesis, and can solve the problems of low space-time yield and high catalyst cost, and achieve a solution with fewer reaction steps, higher yield and less pollution. Effect

Active Publication Date: 2013-04-03
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 (content 98.5%) of dehydrolinalool, 91.0g of methyl acetoacetate, and 4.0g of aluminum isopropoxide into a 500ml pressure-resistant reaction bottle, perform magnetic stirring and heat to an internal temperature of 85°C with an oil bath to keep the reaction Pressure is 1.2MPa reaction 2 hours, gas chromatography analysis dehydrolinalool conversion rate 98.8%. After the reaction is completed, fill it with nitrogen to normal pressure, cool down to 15°C, add dropwise 50ml of 0.5% sodium hydroxide methanol solution, and keep warm for 1.5 hours after dropping. After the isomerization is completed, add acetic acid to adjust the pH value at 6-7. The reaction solution was filtered through a column equipped with a diatomite filter aid using methanol as a solvent, and the filtrate was rectified to obtain 117.3 g of a pseudoionone product of 97.5% (cis-trans sum). The yield of pseudoionone is about 93.1%

Embodiment 2

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

Embodiment 3

[0037] According to the method of embodiment 1, the only difference is that in this embodiment, 91.0 g of methyl acetoacetate is changed into 98.5 g of methyl acetoacetate, and other conditions remain unchanged. The conversion rate of dehydrolinalool was 99.2%, and 114.3 g of pseudoionone products with a content of 97.8% were 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 synthesis method of a compound, belonging to the field of organic synthesis, in particular to a synthesis method of an ionone-series fragrance intermediate. Background technique [0002] Pseudo-ionone and methyl-pseudionone are important intermediates for the synthesis of ionone, and are widely used in the industries of spices, medicine, and food additives. Ionone is a kind of precious spice with woody aroma, which is one of the largest and most important spices in the perfume industry; at the same time, the synthesized β-ionone is an important intermediate for the synthesis of vitamin A and β-carotene. [0003] For a long time, scholars at home and abroad have continued to improve the synthesis process of pseudoionone and its homologues. The main synthesis method is to condense citral with acetone through Aldol under alkaline conditions, and citral is mainly obtained by distillation and purification of litsea cubeba oil and...

Claims

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Application Information

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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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