DE706659C - Process for the preparation of o-oxynaphthoic acids which contain a sulfonic group - Google Patents
Process for the preparation of o-oxynaphthoic acids which contain a sulfonic groupInfo
- Publication number
- DE706659C DE706659C DEI63234D DEI0063234D DE706659C DE 706659 C DE706659 C DE 706659C DE I63234 D DEI63234 D DE I63234D DE I0063234 D DEI0063234 D DE I0063234D DE 706659 C DE706659 C DE 706659C
- Authority
- DE
- Germany
- Prior art keywords
- contain
- preparation
- sulfonic group
- acids
- oxynaphthoic
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von o-Oxynaphthoesäuren, die eine Sulfongruppe enthalten o-Oxynaphthoesäuren, die im Naphthalinkern außerdem noch Sulfongruppen enthalten, sind bisher im allgemeinen nicht bekanntge-,vorden. Dies ist vermutlich darauf zurückzuführen, daß die Einführung einer Carboxylgruppe in Naphthalinderivate, die neben einer Hydroxylgruppe auch noch einen Sulfonrest enthalten, nach der Kolbeschen Synthese sowohl mit als auch ohne Zusatz von Verdünnungsmitteln nicht gelingt.Process for the preparation of o-oxynaphthoic acids containing a sulfonic group contain o-oxynaphthoic acids, which also contain sulfonic groups in the naphthalene nucleus are generally not known to date. This is presumably due to the fact that the introduction of a carboxyl group in naphthalene derivatives, which, in addition to a hydroxyl group, also contain a sulfone radical, according to Kolbe's Synthesis either with or without the addition of diluents does not succeed.
Es wurde nun gefunden, daß man überraschenderweise zu derartigen substituierten o-Oxynaphthoesäuren der allgemeinen Formel gelangt, wenn man Thioäthergruppen enthaltende o-Oxynaphthoesäuren der allgemeinen Formel der Einwirkung von Oxydationsmitteln unterwirft.It has now been found that, surprisingly, such substituted o-oxynaphthoic acids of the general formula can be obtained obtained when o-oxynaphthoic acids of the general formula containing thioether groups subject to the action of oxidizing agents.
Überraschenderweise läßt sich diese Reaktion durchführen, ohne daß dabei Nebenprodukte entstehen, auch wenn man stärkere Oxydationsmittel, wie beispielsweise Wasserstoffsuperoxyd, verwendet. Dieses Ergebnis war nicht voraugzusehen, da ja beispielsweise von Naphtholen bekannt ist, daß sie bereits durch die Einwirkung von gelinden Oxydationsmitteln, wie z. B. Eisenchlorid, in Dinaphthole übergeführt werden. Die bisher unbekannten o-Oxynaphthoesäuren, die im -Molekül außerdem eine Sulfongruppe enthalten, sollen als Zwischenprodukte zur Herstellung von Farbstoffen und Arzneimitteln Verwendung finden.Surprisingly, this reaction can be carried out without thereby by-products arise, even if you use stronger oxidizing agents, such as Hydrogen peroxide is used. This result could not be foreseen, since yes it is known, for example, of naphthols that they are already exposed to them of mild oxidizing agents, such as. B. iron chloride, converted into dinaphthols will. The previously unknown o-oxynaphthoic acids in the molecule also contain a sulfonic group, are intended as intermediates for manufacture of dyes and drugs are used.
Beispiel i ioo Teile cles 2, 3-OxYnaplitliOes.'iure-6-tliiomethyläthers (vgl. Patentschrift 548823) «erden in 5oo Teilen Eisessig suspendiert und aufgekocht. Nach Abkühlung auf 8o° C «erden i io Teile einer 300/,i-..en Wasserstoff -superoxydlösung zugetropft. Unter lebhaftem Aufsieden geht das Sulfit in Lösung. Beim Abkühlen kristallisiert das 2. ; - i )ly"-naphthoesäure-6-methy-l.sulfon aus. Die Ausbeute ist vorzüglich.EXAMPLE 100 parts of 2,3-OxynaplitliOes.'iure-6-tliiomethyläthers (cf. patent 548823) are suspended in 500 parts of glacial acetic acid and boiled. After cooling to 80 ° C., io parts of a 300 /, i - .. en hydrogen peroxide solution are added dropwise. The sulfite dissolves with vigorous boiling. The 2nd crystallizes on cooling; - i) ly "-naphthoic acid-6-methyl-l-sulfone. The yield is excellent.
Die neue Verbindung kristallisiert in schwach gelb gefärbten Kristallen vorn Schmelzpunkt 278°.The new compound crystallizes in pale yellow crystals front melting point 278 °.
Beispiel ioo Teile 2, 3-Oxvnaphtlioesäure-6-thiobutyläther, der durch- Umsetzung des entsprechenden Mercaptans mit Butylhalogenid hergestellt «erden kann, «-erden in 5oo Teilen Eisessig aufgekocht. Das Gemisch wird dann auf etwa ioo° abgekühlt und allmählich mit io2Teilen Perhydrol versetzt. Nach Abklingen der heftigen Reaktion kristallisiert das finit sehr guter Ausbeute gebildete 2, 3-Oxynaphthoes;iure-6-liutylstilfon aus. Es schmilzt bei i87°.Example 100 parts 2, 3-Oxvnaphthlioesäure-6-thiobutylether, the Implementation of the corresponding mercaptan with butyl halide produced «can earth, «- boiled in 500 parts of glacial acetic acid. The mixture is then cooled to about 100 ° and gradually added 10 parts perhydrol. After the violent reaction has subsided the 2, 3-Oxynaphthoes; iure-6-liutylstilfon formed in a finite, very good yield crystallizes the end. It melts at 187 degrees.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI63234D DE706659C (en) | 1938-12-22 | 1938-12-22 | Process for the preparation of o-oxynaphthoic acids which contain a sulfonic group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI63234D DE706659C (en) | 1938-12-22 | 1938-12-22 | Process for the preparation of o-oxynaphthoic acids which contain a sulfonic group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE706659C true DE706659C (en) | 1941-05-31 |
Family
ID=7195863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI63234D Expired DE706659C (en) | 1938-12-22 | 1938-12-22 | Process for the preparation of o-oxynaphthoic acids which contain a sulfonic group |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE706659C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686291A (en) * | 1970-09-03 | 1972-08-22 | Pfizer | Thio derivatives of 2-hydroxy-3-naphthioc acid |
-
1938
- 1938-12-22 DE DEI63234D patent/DE706659C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686291A (en) * | 1970-09-03 | 1972-08-22 | Pfizer | Thio derivatives of 2-hydroxy-3-naphthioc acid |
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