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Method for preparing p-methoxycinnamyl aldehyde spice by using anethole

A technology of methoxycinnamaldehyde and anethole, applied in the field of flavors and fragrances, can solve the problems of only 25% yield, difficult extraction, high price, etc., and achieve high production efficiency, high selectivity, and production low cost effect

Pending Publication Date: 2021-06-01
GUANGXI FORESTRY RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the content of p-methoxycinnamaldehyde in plant raw materials such as plant spice star anise is very low, and it is very difficult to extract from natural edible spice plant star anise, and large production still needs to be produced by artificial synthesis
At present, the literature on the synthesis of p-methoxycinnamaldehyde has been found. For example, in 2013, Mahyari et al. linked graphene to ionic liquids. After loading gold nano-catalysts, they can efficiently catalyze the direct oxidation of 4-methoxycinnamaldehyde into p-methoxycinnamaldehyde. Methoxycinnamaldehyde, but this method must use extremely expensive graphene oxide and gold salt; Zaks et al. found that hydrogen peroxide can oxidize methylstyrene to cinnamaldehyde in water, but the reaction Yield is only 25 percent

Method used

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  • Method for preparing p-methoxycinnamyl aldehyde spice by using anethole
  • Method for preparing p-methoxycinnamyl aldehyde spice by using anethole

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preparation example Construction

[0028] POL-PPh used in the present invention 3 The preparation method is as follows: 1.0g 3V-PPh 3 Dissolve in 10ml of THF, then add 25mg of azobisisobutyronitrile, mix evenly, transfer to a reaction kettle, react at 100°C for 24 hours, and evaporate the solvent in vacuo to obtain white powder POL-PPh3.

[0029] The 3V-PPh 3 The preparation process is as follows: 22mmol of PPh 3 Dissolve it in 30ml THF, and slowly drop it into 4-vinylmagnesium bromide Grignard reagent at 0°C. After the addition is completed, continue the reaction at room temperature for 2 hours. 4 Quench the reaction with Cl solution, extract with excess ethyl acetate, wash the organic phase with saturated brine, dry over anhydrous magnesium sulfate, and finally purify the product with a silica gel column to obtain white 3V-PPh 3 solid.

Embodiment 1

[0031] A kind of method utilizing anethole to prepare p-methoxycinnamaldehyde perfume, comprises the steps:

[0032] (1) Catalyst preparation: under argon atmosphere, 500 mgPOL-PPh 3 , 25 mg PdCl 2 Add it to a 25 mL sealed tube, then add 5 mL of anhydrous THF, react overnight at 25°C, filter, remove the filtrate, wash the filter residue twice with ethyl acetate and ethanol, and collect the solid to obtain POL-PPh 3 @PdCl 2 Catalyst 518 mg;

[0033] (2) Catalytic oxidation reaction: weigh 100 mg POL-PPh in a 250 mL round bottom flask 3 @PdCl 2， Add 10 mmol (1.482 g) of anethole, 50 mmol (0.9 g) of water and 50 mL of toluene, stir well, then slowly add 20 mmol of DDQ (4.54 g) into the round bottom flask, and catalyze the oxidation reaction at room temperature for 1 h;

[0034] (3) Purification: filter the reaction liquid obtained in step (2) through diatomaceous earth, add 20mL water for extraction, and use anhydrous Na 2 SO 4 Dry, concentrate in vacuo to recover the orga...

Embodiment 2

[0037] A kind of method utilizing anethole to prepare p-methoxycinnamaldehyde perfume, comprises the steps:

[0038] (4) Catalyst preparation: under argon atmosphere, 500 mgPOL-PPh 3 , 40mg PdCl 2Add it to a 25 mL sealed tube, then add 5 mL of anhydrous THF, react overnight at 30°C, filter, remove the filtrate, wash the filter residue twice with ethyl acetate and ethanol, and collect the solid to obtain POL-PPh 3 @PdCl 2 Catalyst 532 mg;

[0039] (5) Catalytic oxidation reaction: weigh 100 mg POL-PPh in a 250 mL round bottom flask 3 @PdCl 2， Add 15mmol (2.223 g) of anethole, 45mmol (0.81 g) of water and 50mL of toluene, stir well, then slowly add 30mmol of DDQ (6.81g) into the round bottom flask, and catalyze the oxidation reaction at room temperature for 1.5h;

[0040] (6) Purification: filter the reaction solution obtained in step (2) through diatomaceous earth, add 30mL water for extraction, and use anhydrous Na 2 SO 4 Dry, concentrate in vacuo to recover the organic...

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Abstract

The invention discloses a method for preparing p-methoxycinnamyl aldehyde spice by using anethole, which comprises the following steps of: taking 1 part of POL-PPh3-coated PdCl2 catalyst and 15-20 parts of anethole in parts by mass, adding 2-14 parts of water and 300-500 parts of methylbenzene, uniformly stirring, then adding 45-65 parts of DDQ, and carrying out catalytic oxidation reaction at normal temperature for 0.5-1.5 hours; and filtering through an adsorbent, adding water for extraction, dehydrating and drying, recovering the organic solvent through vacuum concentration, purifying and drying to obtain a faint yellow solid, namely the p-methoxycinnamaldehyde. The method also has the advantages of high yield of the p-methoxycinnamyl aldehyde, mild reaction conditions, high production efficiency, simple process, low production cost, easily available raw materials, less discharge of three wastes and the like, has good social, ecological and economic benefits, and provides an effective way for realizing industrial production of the p-methoxycinnamyl aldehyde perfume.

Description

technical field [0001] The invention relates to the technical field of flavors and fragrances, in particular to a method for preparing p-methoxycinnamaldehyde fragrances from anethole. Background technique [0002] p-Methoxycinnamaldehyde (MCA), white to pale yellow crystalline solid, has a spice and floral aroma, insoluble in water, soluble in organic solvents such as ethanol, is one of the components of plant star anise, and is a nationally recognized food Grade Spice (No. 3567). However, the content of p-methoxycinnamaldehyde in plant raw materials such as plant spice star anise is very low, and it is very difficult to extract from natural food spice plant star anise, and large production still needs to be produced by artificial synthesis. At present, the literature on the synthesis of p-methoxycinnamaldehyde has been found. For example, in 2013, Mahyari et al. linked graphene to ionic liquids. After loading gold nano-catalysts, they can efficiently catalyze the direct o...

Claims

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Application Information

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IPC IPC(8): C07C45/28B01J31/02C07C47/277
CPCC07C45/28B01J31/0269B01J2231/70C07C47/277Y02P20/584
Inventor 杨漓潘英明唐海涛李桂珍蒙秀金谷瑶
Owner GUANGXI FORESTRY RES INST
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