Ionone series spice intermediate synthesis method

The technology of ionone and pseudo-ionone is applied to the synthesis of ionone-based fragrance intermediates and the field of compound synthesis, which can solve the problems of low space-time yield and high catalyst cost, and achieves few reaction steps, high yield and pollution. less effect

Inactive Publication Date: 2015-06-10
QINGDAO HUICHENG PETROCHEM TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Ionone series spice intermediate synthesis method
  • Ionone series spice intermediate synthesis method
  • Ionone series spice intermediate synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Put 100g (content 98.5%) dehydrolinalool, 91.0g methyl acetoacetate, and 4.0g aluminum isopropoxide into a 500ml pressure reaction bottle, carry out magnetic stirring and heat to an internal temperature of 85°C with an oil bath to maintain the reaction pressure It was 1.2MPa and reacted for 2 hours, and the conversion rate of dehydrolinalool was 98.8% according to gas chromatography analysis. 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 ester acid to adjust the pH value at 6-7. The reaction solution was filtered with methanol as a solvent through a column equipped with a diatomaceous earth filter aid, and the filtrate was rectified to obtain 117.3 g of 97.5% (cis and trans sum) pseudoionone products. The yield of pseudoionone is about 93.1%

Embodiment 2

[0038] 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

[0040] 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 the pseudo-violet siphon 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 an ionone series spice intermediate synthesis method, and the ionone series spice intermediates comprise pseudo ionone and methyl pseudo ionone. Dehydrolinalool as a raw material is reacted with formula I compound under the condition of an appropriate catalyst for isomerization reaction for preparation of the pseudo ionone and the methyl pseudo ionone. The ionone series spice intermediate synthesis method is less in reaction steps, high in yield and less in pollution.

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 precious spice with woody aroma, which is one of the largest and most important spices in the perfume industry; the β-violet simultaneously synthesized 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 pseudo-violet siphon and its homologues. The main synthesis method is to condense citral with acetone under Ald0l under alkaline conditions, and citral is mainly obtained by distillation and purification of litsea cubeba oil and ca...

Claims

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Application Information

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IPC IPC(8): C07C49/203C07C45/67
CPCC07C45/67C07C45/69C07C45/78
Inventor 洪龙峰
Owner QINGDAO HUICHENG PETROCHEM TECH
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