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Preparation method of megastigmatrienone

A technology of megadyamarinone and alcohol acetate, applied in the field of spices, can solve the problems such as the difficulty in meeting the requirements of manufacturers, and achieve the effects of low reaction condition requirements, high yield and little physical harm

Active Publication Date: 2014-04-02
广州百花香料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the existing preparation methods of these macrostigmatrienones are difficult to meet the requirements of numerous manufacturers.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0018] The preparation method of macrostigmatrienone of the present invention comprises the following steps:

[0019] (1) Dissolve α-ionol acetate in an organic solvent to form a solution with a concentration of 15%~35% by mass, then add catalyst cuprous chloride and acid to the solution, and then heat the solution at 25°C~40°C Add the oxidant tert-butyl hydroperoxide dropwise to the above mixture under stirring to synthesize 3-oxo-α-ionol acetate, and the reaction time is 4~8h;

[0020] (2), dissolve the 3-oxo-α-ionol acetate obtained in step (1) in an organic solvent to form a solution with a concentration of 20% to 65% by mass, then add catalyst NaOAc, stir and heat to reflux 3~15h, synthesis of macrostigmatrienone crude product;

[0021] (3) Carrying out rectification under reduced pressure to the crude stigmatrienone obtained in the step (2), the target product obtained by the rectification is the stigmatrienone of the present invention.

[0022] Wherein the acid in the...

Embodiment 1

[0034] Example 1: Dissolve 30g of α-ionol acetate in 70ml of acetone, add 3.14g of CuCl, drop in 0.0062g of sulfuric acid, then add dropwise 34.3g of TBHP with a mass percentage concentration of 70% under stirring at 25°C, react for 4 hours, and wash with water. Sodium thiosulfate was quenched, the organic phase was separated, and then the organic solvent was distilled off to obtain 21.3 g of 3-oxo-α-ionol acetate;

[0035] Dissolve the obtained 3-oxo-α-ionol acetate in 76ml of ethylene glycol, add 1.397g of NaOAc, heat to reflux under stirring for 3h, wash the organic phase with water after cooling to neutral, anhydrous Na 2 SO 4 Drying overnight, filtering, and distilling off the organic solvent to obtain the crude stigmatrienone;

[0036]The crude macrostigmatrienone was subjected to vacuum distillation, and the fraction within the boiling range of 120-148°C was collected under a vacuum degree of -0.1-0.09 MPa to obtain 15.6 g of macrostigmatrienone. The content of macr...

Embodiment 2

[0037] Example 2: Dissolve 30g of α-ionol acetate in 90ml of acetonitrile, add 8.38g of CuCl, drop in 0.0031g of sulfuric acid, add dropwise 68.6g of 70% TBHP with stirring at 25°C, and react for 4 hours. Wash with water, quench with sodium thiosulfate, separate the organic phase, then distill off the organic solvent to get 26g of 3-oxo-α-ionol acetate.

[0038] Dissolve the obtained 3-oxo-α-ionol acetate in 70ml of acetone, add 0.426g of NaOAc, heat to reflux under stirring for 10h, wash the organic phase with water after cooling to neutral, anhydrous Na 2 SO 4 Dry overnight, filter, and distill off the organic solvent to obtain the crude macrostigmatrienone.

[0039] The crude macrostigmatrienone was subjected to vacuum distillation, and the fraction within the boiling range of 120-148°C was collected under a vacuum of -0.1-0.09 MPa to obtain 17 g of macrostigmatrienone. The content of macrostigmatrienone detected by GC-MS was 74%, and the total reaction yield was 52%. ...

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Abstract

The invention discloses a preparation method of megastigmatrienone. The method comprises the following steps of: dissolving alpha-ionol acetic ester into an organic solvent, adding cuprous chloride serving as a catalyst and an acid to form a mixed solution, and dropwise adding tert-butyl hydroperoxide serving as an oxidant into the mixed solution for synthesizing 3-oxo-ionol acetic ester; dissolving 3-oxo-ionol acetic ester into an organic solvent, and adding a NaOAc serving as a catalyst to synthesize crude megastigmatrienone; and distilling the crude megastigmatrienone under reduced pressure to obtain megastigmatrienone. In the method, readily-available raw materials are adopted, and a peroxides is taken as an oxidant at an oxidation reaction stage, so that environmental pollution caused by a heavy metal oxidant is avoided. Cuprous chloride is taken as a catalyst, a small amount of acid is dripped, and an oxidation reaction is performed under an acidic condition, so that reaction time is shortened greatly. Basic sodium acetate is taken as a catalyst for performing alkaline hydrolysis on an oxidation product, so that the content of megastigmatrienone and the total yield of the reaction are increased finally.

Description

technical field [0001] The invention relates to the field of perfumes, in particular to a preparation method for synthesizing macrostigmatrienone from alpha-ionol acetate. Background technique [0002] At present, macrostigmatrienone is an important aroma-inducing compound in tobacco, which has tobacco aroma and spicy base rhyme, and is an indispensable spice in cigarette manufacturing. But its content in natural plants is very small. In-depth research on its synthesis has been carried out at home and abroad for a long time. The representative research method for the synthesis of macrostigmatrienone is as follows: [0003] 1. Rowland uses dehydroionone as the raw material, sodium borohydride as the reducing agent, reduces the raw material to dehydroionol, and then rearranges it in acetone with dilute sulfuric acid to obtain 3-hydroxy-4,6,8-gianthan ene, and finally oxidized with active manganese dioxide or chromium trioxide to obtain a mixture of cis-trans isomers of macro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/647C07C45/65
Inventor 喻娟张建斌焦亦正
Owner 广州百花香料股份有限公司
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