CH138866A - Process for the preparation of 4-methyl-6-chloro-oxythionaphten. - Google Patents
Process for the preparation of 4-methyl-6-chloro-oxythionaphten.Info
- Publication number
- CH138866A CH138866A CH138866DA CH138866A CH 138866 A CH138866 A CH 138866A CH 138866D A CH138866D A CH 138866DA CH 138866 A CH138866 A CH 138866A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- chloro
- preparation
- oxythionaphten
- thioglycol
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 4-Methyl-6-ehlor-oaythionaphten. Es wurde gefunden, dass man aus Ver bindungen folgender Formel:
EMI0001.0002
worin X Wasserstoff, Alkyl oder Halogen, Y CN, COOH, C00-Metall und Z Wasserstoff oder Metall bedeutet, durch Erhitzen mit Wasser auf Temperaturen zwischen<B>1000</B> und 200' C, insbesondere bei ungefähr<B>180"</B> C in vorzüglicher Ausbeute Oxythionaphtene erhalten kann, das heisst also,
wenn man solche Thioglykol-o-carbon- säuren oder deren Salze oder Thiogiykol-o- nitrile zur Anwendung bringt, die in o-Stellung zur Carboxylgruppe oder Nitrilgruppe einen weiteren Substituenten vornehmlich einen Alkylrest enthalten. Ist in o-Stellung zur Cyangruppe kein weiterer Substituent vor handen, so tritt keine Oxythionaphtenbildung ein.
Den bekannten Methoden gegenüber be deutet die Umwandlung der in o-Stellung zur Cyangruppe substituierten o-Cyanthioglykol- säuren der Benzolreihe in die entsprechenden Oxythionaphtene in einer Operation nur unter Verwendung von Wasser einen wesentlichen technischen Fortschritt.
Gegenstand dieses Patentes ist ein Ver fahren zur Darstellung des bereits bekannten 4-Methyl-6-chlor-oxythionaphtens, dadurch ge kennzeichnet, dass man 3-lyIethyl-5-chlor-l- thioglykol-2-carbonsäure oder eines ihrer Salze mit Wasser auf Temperaturen über 100 C erhitzt. Die Verbindung dient als Zwischen produkt für die Herstellung von Farbstoffen.
<I>Beispiel:</I> 5 Gewichtsteile 3-Methyl-5-chlorphenyl-l- thioglykol-2-carbonsäure werden mit 40 Teilen Wasser 4 Stunden auf 170-180<B>0 0</B> erhitzt; das entstehende 4-Methyl-6-chlor-oxythionaph- ten wird zur Reinigung mit kalter Sodalösung behandelt, in verdünnter alkoholischer Natron lauge gelöst, filtriert und mit verdünnter Salz säure ausgefällt. An Stelle derfreien Säurekann man auch deren Salze als Ausgangsstoff ver wenden. Die Verbindung dient als Zwischen produkt für die Herstellung von Farbstoffen.
Process for the preparation of 4-methyl-6-chloro-oaythionaphten. It was found that compounds of the following formula can be used:
EMI0001.0002
where X denotes hydrogen, alkyl or halogen, Y denotes CN, COOH, C00 metal and Z denotes hydrogen or metal, by heating with water to temperatures between <B> 1000 </B> and 200 ° C., in particular at approximately <B> 180 "</B> C can obtain oxythionaphtenes in excellent yield, that is to say
if such thioglycol-o-carboxylic acids or their salts or thioglycol-o-nitriles are used which contain a further substituent, primarily an alkyl radical, in the o-position to the carboxyl group or nitrile group. If there is no further substituent in the o-position to the cyano group, no oxythionaphthene formation occurs.
In contrast to the known methods, the conversion of the o-cyanothioglycolic acids of the benzene series, substituted in the o-position to the cyano group, into the corresponding oxythionaphthens in one operation using only water, represents a significant technical advance.
The subject of this patent is a process for the preparation of the already known 4-methyl-6-chloro-oxythionaphthene, characterized in that 3-lyIethyl-5-chloro-1-thioglycol-2-carboxylic acid or one of its salts is added with water Temperatures over 100 C heated. The compound serves as an intermediate product for the manufacture of dyes.
<I> Example: </I> 5 parts by weight of 3-methyl-5-chlorophenyl-1-thioglycol-2-carboxylic acid are heated with 40 parts of water to 170-180 0 0 for 4 hours; the resulting 4-methyl-6-chloro-oxythionaphthene is cleaned with cold soda solution, dissolved in dilute alcoholic sodium hydroxide solution, filtered and precipitated with dilute hydrochloric acid. Instead of the free acid, its salts can also be used as starting material. The compound serves as an intermediate product for the manufacture of dyes.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE138866X | 1927-10-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH138866A true CH138866A (en) | 1930-03-31 |
Family
ID=5667499
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH138866D CH138866A (en) | 1927-10-17 | 1928-09-24 | Process for the preparation of 4-methyl-6-chloro-oxythionaphten. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH138866A (en) |
-
1928
- 1928-09-24 CH CH138866D patent/CH138866A/en unknown
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