CH169041A - Process for the preparation of the benzoic acid ester of crotonaldehyde cyanohydrin. - Google Patents
Process for the preparation of the benzoic acid ester of crotonaldehyde cyanohydrin.Info
- Publication number
- CH169041A CH169041A CH169041DA CH169041A CH 169041 A CH169041 A CH 169041A CH 169041D A CH169041D A CH 169041DA CH 169041 A CH169041 A CH 169041A
- Authority
- CH
- Switzerland
- Prior art keywords
- crotonaldehyde
- acid ester
- benzoic acid
- cyanohydrin
- preparation
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung des Benzoesäureesters des Crotonaldehydeyanhydrines. Es wurde gefunden, dass man Säureester von Cyanhydrinen ungesättigter, alipliatischer Aldehyde in guter Ausbeute und auf tech nisch einfache Weise herstellen kann, wenn man auf ein Gemisch von einem ungesättigten, alipliatischen Aldehyd und einem Aroylhaloid beziehungsweise dessen Substitutionsprodukte Cyankalium beziehungsweise Oyannatrium- lösung einwirken lässt.
Zweckmässig wird diese Reaktion in Gegenwart eines Lösungs mittels und bei niedriger Temperatur, wie zum Beispiel unter 5 C, ausgeführt. Die Reaktion erfolgt gemäss der Gleichung
EMI0001.0012
Ri, R2 und Ra = Wasserstoff oder Alkyl, R4 = Aryl beziehungsweise substituiertes tlryl, Me = Alkalimetall.
(xegenstand des vorliegenden Patentes ist nun ein Verfahren zur Darstellung des Ben- zoesäureesters des Crotonaldeliydcyanhydrins, welches dadurch gekennzeichnet ist, dass man Crotonaldehyd, ein Alkalicyanid und Bellzoyl- chlorid in Gegenwart von Wasser aufeinander einwirken lässt.
Es empfiehlt sich, die Reaktion in Gegen- wart von Benzol und bei tiefer Temperatur durchzuführen.
Das neue Produkt schmilzt zwischen 30 und<B>31'</B> und siedet unter 4 mm Druck bei 128-1290. Es soll als Insektizid verwendet werden.
<I>Beispiel:</I> In ein Geinisch von 35 Gewichtsteilen Crotonaldehyd, 35 Gewichtsteilen Benzol und 70,3 Gewichtsteilen Benzoylchlorid wird unter lebhaftem Rühren bei -10 eine Lösung von 28 Gewichtsteilen Cyannatrium in 56 Gewichts teilen Wasser eintropfen gelassen. Nachdem alles eingetragen und das Reaktionsgemisch von der Kochsalzlösung getrennt ist, wird die abgeschiedene benzolische Lösung über Chlorcalcium getrocknet und im Vakuum destilliert.
In nahezu quantitativer Ausbeute wird der bei 128-129 4 mm siedende Benzoesäureester des Crotonaldehydcyan- hydrins erhalten, der nach dem Erstarren bei 30-310 schmilzt.
Process for the preparation of the benzoic acid ester of crotonaldehyde anhydrin. It has been found that acid esters of cyanohydrins of unsaturated, aliphatic aldehydes can be produced in good yield and in a technically simple manner if a mixture of an unsaturated, aliphatic aldehyde and an aroyl halide or its substitution products are allowed to act on cyanide potassium or oyannodium solution.
This reaction is expediently carried out in the presence of a solvent and at low temperature, such as below 5 ° C., for example. The reaction takes place according to the equation
EMI0001.0012
Ri, R2 and Ra = hydrogen or alkyl, R4 = aryl or substituted tlryl, Me = alkali metal.
(The subject of the present patent is a process for the preparation of the benzoic acid ester of crotonaldelium cyanohydrin, which is characterized in that crotonaldehyde, an alkali metal cyanide and bellzoyl chloride are allowed to act on one another in the presence of water.
It is advisable to carry out the reaction in the presence of benzene and at low temperature.
The new product melts between 30 and <B> 31 '</B> and boils at 128-1290 under 4 mm pressure. It is said to be used as an insecticide.
<I> Example: </I> A solution of 28 parts by weight of cyan sodium in 56 parts by weight of water is dripped into a mixture of 35 parts by weight of crotonaldehyde, 35 parts by weight of benzene and 70.3 parts by weight of benzoyl chloride with vigorous stirring at -10. After everything has been entered and the reaction mixture has been separated from the saline solution, the separated benzene solution is dried over calcium chloride and distilled in vacuo.
The benzoic acid ester of crotonaldehyde cyanohydrin which boils at 128-129 4 mm and melts at 30-310 after solidification is obtained in almost quantitative yield.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169041X | 1932-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169041A true CH169041A (en) | 1934-05-15 |
Family
ID=5687568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169041D CH169041A (en) | 1932-08-10 | 1933-05-19 | Process for the preparation of the benzoic acid ester of crotonaldehyde cyanohydrin. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169041A (en) |
-
1933
- 1933-05-19 CH CH169041D patent/CH169041A/en unknown
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