CH475184A - Process for the preparation of phenyl carboxylic acid esters - Google Patents

Process for the preparation of phenyl carboxylic acid esters

Info

Publication number
CH475184A
CH475184A CH118269A CH118269A CH475184A CH 475184 A CH475184 A CH 475184A CH 118269 A CH118269 A CH 118269A CH 118269 A CH118269 A CH 118269A CH 475184 A CH475184 A CH 475184A
Authority
CH
Switzerland
Prior art keywords
formula
preparation
carboxylic acid
acid esters
methyl acrylate
Prior art date
Application number
CH118269A
Other languages
German (de)
Inventor
Ludwig Dr Eue
Helmuth Dr Hack
Kurt Dr Westphal
Richard Dr Wegler
Original Assignee
Bayer Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE1542777A external-priority patent/DE1542777C3/en
Application filed by Bayer Ag filed Critical Bayer Ag
Priority to CH118269A priority Critical patent/CH475184A/en
Priority claimed from CH729166A external-priority patent/CH474954A/en
Publication of CH475184A publication Critical patent/CH475184A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  



  Verfahren zur Herstellung von   Phenylcarbonsäureestern   
Die vorliegende Erfindung betrifft die Herstellung von Phenylcarbonsäureestern der Formel I
EMI1.1     
 und ist dadurch gekennzeichnet, dass man Amine der Formel II
EMI1.2     
 zu Diazoverbindungen der Formel III
EMI1.3     
 diazotiert und letztere mit Acrylsäuremethylester umsetzt.



   Das Verfahren wird nachfolgend anhand eines For  melschemas    erläutert: 1. Stufe: 2. Stufe:
EMI1.4     

In der 1. Stufe werden die Amine diazotiert, zweckmässigerweise in Gegenwart von Wasser und Salzsäure bei Temperaturen von 0-20   OC.   



   In der 2. Stufe werden die in der 1. Stufe erhaltenen Diazoverbindungen mit Acrylsäuremethylester umgesetzt, der zweckmässigerweise gelöst in einem mit Wasser mischbaren Lösungsmittel, wie Aceton, vorgelegt wird.



  Die Umsetzung der Diazoverbindungen mit dem Acrylsäuremethylester erfolgt vorzugsweise bei Temperaturen zwischen 10 und 60   "C.   



   Die erhaltenen Verbindungen der Formel I weisen starke selektive herbizide Eigenschaften auf und lassen sich daher hervorragend als aktive Komponente in herbiziden Mitteln verwenden. Bei der Bekämpfung von Unkraut im Getreide haben sie eine höhere selektive herbizide Wirkung als beispielsweise   4-Chlor-2-butinyl-    N-(3-chlorphenyl)-carbamat, wenn sie nach dem postemergence-Verfahren angewendet werden. Darüber hinaus haben sie jedoch auch eine gute selektive herbizide Wirkung bei der Verwendung im pre-emergence-Verfahren, bei welchem das vorgenannte 4-Chlor-2-butinyl N-(3-chlorphenyl)-carbamat kaum wirksam ist.



   Bevorzugt werden   a-Chlor-ss-(m-chlorphenyl-)    propionsäuremethylester und a-Chlor-ss-(p-chlorphenyl-) propionsäuremethylester hergestellt, da diese Verbindungen als selektive herbizide Mittel besonders wirksam sind.



   Beispiel
63,8 g m-Chloranilin werden in 300   cm3    Wasser und 100 cm3 konzentrierter Salzsäure heiss gelöst und nach dem Kühlen mit Eis diazotiert. Die Diazolösung wird mit Natriumacetat abgestumpft, geklärt und in eine etwa 40   OC    warme Lösung von 14 g CuCl2   21130    und 43 g Acrylsäuremethylester in   11/2 1    Aceton eingerührt. Nach dem Aufhören der Stickstoffentwicklung wird mit Wasser verdünnt und ausgeäthert. Der Rückstand der ätherischen Phase siedet bei 0,08 mm und 106   "C.    Man erhält 46,7 g   a-Chlor-p-(m-chlorphenyl-)    propionsäuremethylester.



  



  Process for the preparation of phenyl carboxylic acid esters
The present invention relates to the preparation of phenyl carboxylic acid esters of the formula I.
EMI1.1
 and is characterized in that amines of the formula II
EMI1.2
 to diazo compounds of the formula III
EMI1.3
 diazotized and the latter is reacted with methyl acrylate.



   The process is explained below using a formula: 1st stage: 2nd stage:
EMI1.4

In the 1st stage, the amines are diazotized, conveniently in the presence of water and hydrochloric acid at temperatures of 0-20.degree.



   In the 2nd stage, the diazo compounds obtained in the 1st stage are reacted with methyl acrylate, which is expediently dissolved in a water-miscible solvent such as acetone.



  The reaction of the diazo compounds with the methyl acrylate is preferably carried out at temperatures between 10 and 60 ° C.



   The compounds of the formula I obtained have strong selective herbicidal properties and can therefore be used outstandingly as active components in herbicidal compositions. When combating weeds in cereals, they have a higher selective herbicidal effect than, for example, 4-chloro-2-butynyl-N- (3-chlorophenyl) carbamate when they are used according to the post-emergence method. In addition, however, they also have a good selective herbicidal action when used in the pre-emergence process, in which the aforementioned 4-chloro-2-butynyl N- (3-chlorophenyl) carbamate is hardly effective.



   Methyl a-chloro-ss- (m-chlorophenyl) propionate and methyl a-chloro-ss- (p-chlorophenyl) propionate are preferably prepared, since these compounds are particularly effective as selective herbicidal agents.



   example
63.8 g of m-chloroaniline are dissolved hot in 300 cm3 of water and 100 cm3 of concentrated hydrochloric acid and, after cooling, diazotized with ice. The diazo solution is blunted with sodium acetate, clarified and stirred into a solution of 14 g CuCl2 21130 and 43 g of methyl acrylate in 11/2 1 acetone at about 40 ° C. After the evolution of nitrogen has ceased, it is diluted with water and extracted with ether. The residue of the ethereal phase boils at 0.08 mm and 106 "C. 46.7 g of methyl a-chloro-p- (m-chlorophenyl) propionate are obtained.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von Phenylcarbonsäureestern der Formel I EMI2.1 dadurch gekennzeichnet, dass man Amine der Formel II EMI2.2 zu Diazoverbindungen der Formel III EMI2.3 diazotiert und letztere mit Acrylsäuremethylester umsetzt. PATENT CLAIM Process for the preparation of phenyl carboxylic acid esters of the formula I. EMI2.1 characterized in that amines of the formula II EMI2.2 to diazo compounds of the formula III EMI2.3 diazotized and the latter is reacted with methyl acrylate. UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI2.4 herstellt. SUBCLAIMS 1. The method according to claim, characterized in that a compound of the formula EMI2.4 manufactures. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI2.5 herstellt. 2. The method according to claim, characterized in that a compound of the formula EMI2.5 manufactures. 3. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Diazotierung in Gegenwart von Wasser und Salzsäure bei Temperaturen von 0-20 OC durchführt. 3. The method according to claim, characterized in that the diazotization is carried out in the presence of water and hydrochloric acid at temperatures of 0-20 ° C. 4. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass der Acrylsäuremethylester in einem mit Wasser mischbaren Lösungsmittel, vorzugsweise Aceton, gelöst vorgelegt wird. 4. The method according to claim, characterized in that the methyl acrylate is presented dissolved in a water-miscible solvent, preferably acetone. 5. Verfahren nach Patentanspruch oder Unteranspruch 4, dadurch gekennzeichnet, dass man die Umsetzung der Diazoverbindungen mit dem Acrylsäuremethylester bei Temperaturen zwischen 10 und 60 OC durchführt. 5. The method according to claim or dependent claim 4, characterized in that the reaction of the diazo compounds with the methyl acrylate is carried out at temperatures between 10 and 60 ° C.
CH118269A 1965-04-17 1966-05-20 Process for the preparation of phenyl carboxylic acid esters CH475184A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH118269A CH475184A (en) 1965-04-17 1966-05-20 Process for the preparation of phenyl carboxylic acid esters

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1542777A DE1542777C3 (en) 1965-04-17 1965-04-17 Methyl α-chloro-β- (4-chlorophenyl) propionate and herbicides containing a α-chloro-β-phenylpropionic acid derivative
CH118269A CH475184A (en) 1965-04-17 1966-05-20 Process for the preparation of phenyl carboxylic acid esters
CH729166A CH474954A (en) 1965-04-17 1966-05-20 Selectively herbicidal agent

Publications (1)

Publication Number Publication Date
CH475184A true CH475184A (en) 1969-07-15

Family

ID=27172766

Family Applications (1)

Application Number Title Priority Date Filing Date
CH118269A CH475184A (en) 1965-04-17 1966-05-20 Process for the preparation of phenyl carboxylic acid esters

Country Status (1)

Country Link
CH (1) CH475184A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0156770A1 (en) * 1984-03-27 1985-10-02 Ciba-Geigy Ag Stilbene derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0156770A1 (en) * 1984-03-27 1985-10-02 Ciba-Geigy Ag Stilbene derivatives

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