4-methyl cinnamic acid methyl ester

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Product
4-methyl cinnamic acid methyl ester
Posting date : Mar 14, 2019
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Free Member Scince Mar 14, 2019
FOB Price
1000
Min. Order Quantity
1kg
Supply Abillity
1000kg
Port
Hongkong
Payment Terms
TT
Package
Foil bag
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Eason
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Product Detail
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Place of Origin
China [CN]
Brand Name
Landmarkind
HS-CODE
2811-19
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Package
Foil bag
Detailed Description
4-methyl cinnamic acid methyl ester
Name
4-methyl cinnamic acid methyl ester
Molecular Structure
Alias
METHYL 4-METHYLCINNAMATE
Methyl trans-4-methylcinnamate
Methyl 3-(p-tolyl)acrylate
methyl (E)-3-(4-methylphenyl)prop-2-enoate
 
 
 
 
 
CAS.No
20754-20-5
Molecular formula
C11H12O2
Molecular weight
176.21
Density
1.057g/cm3
Melting Point
60-61 degree C
Boiling point
272.9 degree C at 760 mmHg
Appearance
White to light yellow crystalline powder
Acid value(mgKOH/g)
Is no more than 3.0
 
4-methyl cinnamic acid methyl ester is a pharmaceutical intermediate. It is mainly used for the synthesis of methyl bromomethylcinnamate, the upstream raw material of the antithrombotic drug Ozagrel sodium. Methyl p-methylcinnamate is brominated by N-bromosuccinimide to obtain methyl p-bromomethylcinnamate, methyl p-bromomethylcinnamate in ionic liquid N-n-butylpyridine tetrafluoroboron The acid salt was lyophilized with imidazole at room temperature and then hydrolyzed to obtain an antithrombotic drug, ozagrel sodium, with a total yield of 67%. Methyl p-methylcinnamate is first reacted with p-methylbenzaldehyde and malonic acid to form p-methylcinnamic acid, which is then esterified with p-methylcinnamic acid and methanol to form methyl p-methylcinnamate.
 
The process for preparing cinnamate by condensation of benzoquinone with acetate is known as the Claisen-Schmidt condensation reaction. The main methods for preparing cinnamate by Claisen-Schmidt reaction are as follows:
1. Prepared with anhydrous ethanol as solvent and 10% NaOH as catalyst, but the method has long reaction time and side reaction.
Should be more, product yield is low, production efficiency is poor.
  • The acetic acid ester is used as a solvent and the sodium alkoxide is used as a catalyst to condense. This method improves the product yield, but the post-treatment is complicated and the purification is difficult. In the preparation, a large excess of the raw material ratio of the acetate is used, and the excess acetate is prone to ester condensation reaction under a strong basic catalyst, and a large amount of by-products are formed, which leads to difficulty in product purification.
 
In addition, methyl methyl cinnamate is mostly obtained by reacting p-methylbenzaldehyde with acetic anhydride or malonic acid to obtain p-methylcinnamic acid, followed by esterification with methanol to obtain methyl p-methylcinnamate. Synthetic method. Because of the existing process steps, poor production conditions, low product yield, high cost and serious pollution, it does not meet the requirements of green production.
 
Now, A new method for preparing 4-methyl cinnamic acid methyl ester comprises the following steps:
1) stirring and mixing with ethylene glycol dimethyl ether as a solvent and lithium diisopropylamide as a catalyst, and then stirring slowly Add p-methylbenzaldehyde dropwise, keep the temperature below 5 degree C
  • After the dropwise addition, keep the reaction at 0 degree C- 10 degree C for 3-6h, slowly add 10% by mass of sulfuric acid to make The PH of the reaction solution is adjusted between 6.8 and 7.2
  • The above solution is separated into an organic layer, and the solvent and excess p-methylbenzaldehyde are recovered under reduced pressure to obtain a white solid, which is washed with water and dried to give a crude product. Recrystallization from absolute ethanol gave 4-methyl cinnamic acid methyl ester.
 
The invention has the advantages of low raw material cost, mild reaction condition, and methyl p-methylcinnamate obtained by one-step reaction, and the method is simple, easy to operate, high in yield, stable and reliable in product quality, and non-polluting to the environment, is a kind of green The method of synthesizing fragrance.
 
 
 
 
 

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