CH211203A - Process for the preparation of methyl-p-tolylcarbinol-camphoric acid sodium. - Google Patents
Process for the preparation of methyl-p-tolylcarbinol-camphoric acid sodium.Info
- Publication number
- CH211203A CH211203A CH211203DA CH211203A CH 211203 A CH211203 A CH 211203A CH 211203D A CH211203D A CH 211203DA CH 211203 A CH211203 A CH 211203A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- tolylcarbinol
- sodium
- preparation
- acid sodium
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
Description
Verfahren zur Herstellung von methyl-p-tolylearbinol-eamphersaurem Natrium. Es ist bekannt, dass das ätherische 01 der 'remoe-Lawak-Droge und insbesondere das zu etwa 5 % darin enthaltene Methyl-p-tolyl- carbinol gallesekretionssteigernde Wirkun gen besitzt. Der therapeutischen Anwendung dieses Alkohols steht aber seine Wasser unlöslichkeit entgegen, die insbesondere eine parenterale Anwendung unmöglich macht.
Es wurde nun gefunden, dass man eine neue, leicht wasserlösliche Verbindung des 3Iethyl-p-tolylcarbinols dadurch herstellen kann, dass man Natrium-methyl-p-tolylearbi- nolat mit Camphersäureanhydrid in einem organischen Lösungsmittel umsetzt. Das Na trium - methyl - p - tolylcarbinolat kann dabei aus Natrium und 112ethyl-p-tolylcarbinol in Gegenwart von Camphersäureanhydrid her gestellt werden.
Man erhält so das methyl- p-tolylcarbinolcamphersaure Natrium, ein weisses hygroskopisches Pulver, das sich bei Zimmertemperatur in Wasser zu 40 bis 50 löst.
Die neue Verbindung ist ebenso galletrei- bend wie das ihr zu Grunde liegende Methyl- p-tolylcarbinol. Im Gegensatz zu diesem ist sie aber bis zu 40 % in Wasser löslich. Ihre Lösung enthält das wirksame Methyl-p-tolyl- carbinol in leicht abspaltbarer und infolge dessen hochwirksamer Form. Sie kann daher zur Steigerung der Gallesekretion verwendet werden.
Anderseits kann sie zur Herstellung an derer Salze der Methyl-p-tolylcarbinol-cam- phersäure mit anorganischen oder organi schen Basen dienen. Zu diesem Zweck wird aus dem carbinolcamphersauren Natrium, z. B. durch Schwefelsäure, die Carbinolcam- phersäure in. Freiheit gesetzt und diese mit anorganischen Basen, z. B. Ammoniak, an dern Alkalien, Erdalkalien oder organischen Basen, z.
B. Diäthanolamin oder Äthylen diamin neutralisiert. Beispiel: Zu einer angewärmten benzolischen Lö sung von 18,2 g Camphersäureanhydrid wird eine benzolische Lösung von 13,6 g Dlethyl- p-tolylcarbinol, in der 2,3 g Natrium gelöst worden sind, zugefügt. Nach dem Erkalten des Lösungsgemisches wird Wasser zugesetzt und die wässrige Schicht, die das metbyl-p- tolylcarbinol-camphersaure Natrium enthält, abgetrennt.
Process for the preparation of methyl-p-tolylearbinol-amphersaurem sodium. It is known that the essential oil of the 'remoe Lawak drug and in particular the approximately 5% methyl-p-tolyl-carbinol contained in it has bile secretion-increasing effects. The therapeutic use of this alcohol stands in the way of its insolubility in water, which makes parenteral use in particular impossible.
It has now been found that a new, easily water-soluble compound of 3Iethyl-p-tolylcarbinol can be produced by reacting sodium methyl-p-tolylearbinolate with camphoric anhydride in an organic solvent. The sodium - methyl - p - tolylcarbinolate can be made from sodium and 112ethyl-p-tolylcarbinol in the presence of camphoric anhydride.
This gives sodium methyl-p-tolylcarbinolcamphoric acid, a white, hygroscopic powder which dissolves 40 to 50% in water at room temperature.
The new compound is just as cholagogue as the methyl-p-tolylcarbinol on which it is based. In contrast to this, however, it is up to 40% soluble in water. Your solution contains the effective methyl-p-tolyl-carbinol in an easily cleavable and therefore highly effective form. It can therefore be used to increase bile secretion.
On the other hand, it can be used to produce other salts of methyl-p-tolylcarbinol camper acid with inorganic or organic bases. For this purpose, sodium carbinolcamphoric acid, e.g. B. by sulfuric acid, the Carbinolcam- phersäure in. Freedom and this with inorganic bases, z. B. ammonia, on dern alkalis, alkaline earths or organic bases, z.
B. diethanolamine or ethylene diamine neutralized. Example: A benzene solution of 13.6 g of methyl-p-tolylcarbinol, in which 2.3 g of sodium has been dissolved, is added to a heated benzene solution of 18.2 g of camphoric anhydride. After the mixed solution has cooled, water is added and the aqueous layer, which contains the methyl-p-tolylcarbinol-camphoric acid sodium, is separated off.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH211203T | 1938-08-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH211203A true CH211203A (en) | 1940-08-31 |
Family
ID=4447231
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH211203D CH211203A (en) | 1938-08-12 | 1938-08-12 | Process for the preparation of methyl-p-tolylcarbinol-camphoric acid sodium. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH211203A (en) |
-
1938
- 1938-08-12 CH CH211203D patent/CH211203A/en unknown
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