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A kind of method of synthesizing p-tert-butylphenylpropionaldehyde

A technology for tert-butyl phenylpropionaldehyde and p-tert-butyl aldehyde, which is applied in the field of synthesizing p-tert-butyl phenylpropionaldehyde, can solve the problems of difficult suction filtration, high viscosity, difficult handling, etc., and achieves simple post-processing, little pollution, The effect of suction filtration with high viscosity

Active Publication Date: 2022-04-19
KUNSHAN YAXIANG SPICEL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are the following disadvantages. The Friedel-Crafts reaction uses a large amount of titanium tetrachloride to produce a large amount of waste acid, which causes corrosion and "three wastes" treatment problems; at the same time, the titanium chloride particles generated are relatively fine, and after mixing with water, they form "slime" , high viscosity, difficult to filter

Method used

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  • A kind of method of synthesizing p-tert-butylphenylpropionaldehyde
  • A kind of method of synthesizing p-tert-butylphenylpropionaldehyde
  • A kind of method of synthesizing p-tert-butylphenylpropionaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Weigh 10g (0.062mol) of p-tert-butylbenzaldehyde and 3.26g (0.072mol) of acetaldehyde and dissolve it in toluene, then add 4g (0.1mol) of NaOH, reflux and distill off water, after the reaction is completed, adjust it with 10% hydrochloric acid PH = between 5 and 6, and then extracted to obtain 12 g of a mixture containing 3-(4-(tert-butyl)phenyl)acrylaldehyde. Dissolve 3-(4-(tert-butyl basic) phenyl) allyl aldehyde in toluene, ethylene glycol 20g and add 1g of p-toluenesulfonic acid under the catalysis, fractionate the water, after the reaction, wash the substrate with 5% Na 2 CO 3 The aqueous solution was washed 1-3 times, and then back-extracted once with ether, and the organic layers were combined to obtain 15 g of the mixture. Dissolve 15 g of the mixture with ethanol solution, add 2 g of palladium carbon, put it into a reaction bottle, replace the gas in the bottle with hydrogen, put a hydrogen balloon on it, and react overnight. After the reaction was complete, ...

Embodiment 2

[0019] Weigh 150g of p-tert-butylbenzaldehyde and 48.6g of acetaldehyde and dissolve it in 500ml of toluene, then add 45g (0.1mol) of NaOH, reflux and distill off water, after the reaction is completed, adjust the pH to between 5 and 6 with 10% hydrochloric acid , and then extracted to obtain 178 g of a mixture containing 3-(4-(tert-butyl)phenyl)acrylaldehyde. Dissolve 3-(4-(tert-butyl basic) phenyl) allyl aldehyde in toluene, 65 g of ethylene glycol and add 6 g of p-toluenesulfonic acid under the catalysis, and distill off water. After the reaction, the substrate is washed with 5% Na 2 CO 3 The aqueous solution was washed 1-3 times, and then back-extracted once with ether, and the organic layers were combined to obtain 175 g of the mixture. Dissolve 175g of the mixture with ethanol solution, add 15g of palladium carbon, put it into a reaction kettle, replace the gas in the bottle with hydrogen, pressurize to 3-7MPa, and react overnight. After the reaction was complete, the ...

Embodiment 3

[0021] Weigh 1.5kg of p-tert-butylbenzaldehyde and 611g of acetaldehyde and dissolve it in toluene, then add NaOH, reflux and distill off water, after the reaction is completed, use 10% hydrochloric acid to adjust the pH to between 5 and 6, and then extract to obtain 1.68 Kg contains 3-(4-(tert-butyl)phenyl)allyl aldehyde mixture. Dissolve 3-(4-(tert-butyl)phenyl)acrylaldehyde in toluene and 600ml of ethylene glycol, then add 48g (3%) of p-toluenesulfonic acid to catalyze, fractionate water, and remove the bottom after the reaction 5% Na 2 CO 3 The aqueous solution was washed 1-3 times, and then back-extracted once with ether, and the organic layers were combined to obtain 1.72Kg of the mixture. Dissolve 1.72kg of the mixture with ethanol solution, add 150g of palladium carbon, put it into the reaction kettle, replace the gas in the bottle with hydrogen, pressurize to 6-7MPa and react overnight. After the reaction was complete, the palladium carbon was filtered off, and the...

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Abstract

The invention discloses a method for synthesizing p-tert-butylphenylpropionaldehyde, which is carried out according to the following reaction formula: specifically, the steps are as follows: the unsaturated aldehyde is generated by the Claisen-Schmidt condensation reaction of formula I under alkaline conditions And the step of obtaining formula II; dissolving formula II in toluene and ethylene glycol under the action of a catalyst, fractionating water, and condensing to generate the step of formula III; dissolving formula III in a solvent, adding a catalyst, and feeding hydrogen under pressure Reducing the double bond to obtain the step of formula IV; hydrolyzing the acetal of formula IV into aldehyde under acidic conditions to obtain the step of formula V of p-tert-butylphenylpropionaldehyde. The method for synthesizing p-tert-butyl propionaldehyde of the present invention, compared with the prior art using Krafts acylation reaction, has mild conditions, strong selectivity of Claisen-Schmidt condensation reaction, high condensation unity, and avoids A large amount of highly corrosive titanium tetrachloride is used, causing serious pollution problems. The reaction synthesis of the invention has little pollution, simple aftertreatment, and meets the requirements of modern green production.

Description

technical field [0001] The invention relates to the field of food additives, in particular to a method for synthesizing p-tert-butylphenylpropionaldehyde. Background technique [0002] p-tert-butylphenylpropionaldehyde, also known as Bojie red aldehyde, is an important fragrance agent. The synthesis of existing technology p-tert-butylphenylpropionaldehyde is to utilize tert-butylbenzene and propylene glycol diacetate in TiCl 4 Carry out Friedel-Crafts reaction under catalysis to obtain propylene p-tert-butylphenylacetate, and then obtain p-tert-butylphenylpropionaldehyde in alcoholysis. There are the following disadvantages. The Friedel-Crafts reaction uses a large amount of titanium tetrachloride to produce a large amount of waste acid, which causes corrosion and "three wastes" treatment problems; at the same time, the titanium chloride particles generated are relatively fine, and after mixing with water, they form "slime" , high viscosity, difficult to filter. Contents...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/59C07C47/228C07C45/74C07C47/232C07D317/12
CPCC07C45/59C07C45/74C07D317/12C07C47/228C07C47/232
Inventor 周军学陈清
Owner KUNSHAN YAXIANG SPICEL CO LTD
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