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Method for synthesizing 3-(4-tert-butylphenyl)propionaldehyde

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

Active Publication Date: 2018-04-24
KUNSHAN YAXIANG SPICEL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Method for synthesizing 3-(4-tert-butylphenyl)propionaldehyde
  • Method for synthesizing 3-(4-tert-butylphenyl)propionaldehyde
  • Method for synthesizing 3-(4-tert-butylphenyl)propionaldehyde

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 3-(4-tert-butylphenyl)propionaldehyde. The method is executed according to reaction formulas as shown in the description and specifically comprises following steps: a compound shown as the formula I is subjected to Claisen-Schmidt condensation reaction, unsaturated aldehydes are produced, and a compound shown as the formula II is obtained; the compound shown as the formula II is dissolved in toluene and ethanediol and subjected to fractional distillation and water discharge under the action of a catalyst, and a compound shown as the formula IIIis produced through condensation; the compound shown as the formula III is dissolved in a solvent, then the catalyst is added, hydrogen is introduced under pressurizing action to reduce double bonds,and a compound shown as the formula IV is obtained; acetal shown as the formula IV is hydrolyzed under the acidic condition to form aldehyde, and 3-(4-tert-butylphenyl)propionaldehyde shown as the formula V is obtained. Compared with Friedel-Crafts acylation reaction in the prior art, the method for synthesizing 3-(4-tert-butylphenyl)propionaldehyde has the advantages as follows: conditions are mild, the Claisen-Schmidt condensation reaction is high in selectivity, unicity of condensation is high, and the problem of severe pollution caused by high consumption of strong-corrosion titanium tetrachloride is solved. The reaction synthesis is low-pollution, aftertreatment is simple, and the requirement of modern green production is met.

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 Applications(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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