DE589145C - Process for the preparation of pyrenoyl-o-benzoic acids - Google Patents
Process for the preparation of pyrenoyl-o-benzoic acidsInfo
- Publication number
- DE589145C DE589145C DEI44001D DEI0044001D DE589145C DE 589145 C DE589145 C DE 589145C DE I44001 D DEI44001 D DE I44001D DE I0044001 D DEI0044001 D DE I0044001D DE 589145 C DE589145 C DE 589145C
- Authority
- DE
- Germany
- Prior art keywords
- pyrenoyl
- benzoic acids
- preparation
- weight
- parts
- 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
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Pyrenoyl-o-benzoesäuren Es wurde gefunden, daß Pyren sich mit Phthalsäureanhydrid und seinen Halogensubstitutionsprodukten in glatter Weise zu den entsprechenden Pyrenoyl-o-benzoesäuren, welchen wahrscheinlich die allgemeine For-Mel zukominen dürfte (X - H oder Substituenten), kondensieren läßt. Die Kondensation wird in an sich bekannter Weise mit einem Aluminiumhalogenid in organischen Lösungsmitteln bei Temperaturen, die 8o bis ioo° nicht übersteigen, ausgeführt, wobei sich Benzol, Mono-, Di- und Trichlorbenzol als für die Ausbeute am geeignetesten erwiesen haben. Die neuen Körper sind wertvolle Zwischenprodukte für Farbstoffe.Process for the preparation of pyrenoyl-o-benzoic acids It has been found that pyrene reacts smoothly with phthalic anhydride and its halogen substitution products to the corresponding pyrenoyl-o-benzoic acids, which probably have the general formula zukominen is likely (X - H or substituents), can condense. The condensation is carried out in a manner known per se with an aluminum halide in organic solvents at temperatures not exceeding 80 ° to 100 °, benzene, mono-, di- and trichlorobenzene having proven to be the most suitable for the yield. The new bodies are valuable intermediates for dyes.
Beispiel i 72o Gewichtsteile Pyren werden in 45o Gewichtsteilen Chlorbenzol gelöst, 525 Gewichtsteile Phthalsäureanhydrid zugefügt und io5o Gewichtsteile Aluminiumchlorid nach und nach eingetragen. Das Reaktionsgemisch färbt sich dabei rotviolett, :und ein dunkler Körper fällt sandig aus. Nachdem alles Aluminiumchlorid eingetragen ist, erhitzt man noch 2 Stunden auf 55 bis 65°. Man trägt dann in Eis und Salzsäure ein, bläst das Chlorbenzol mit Dampf ab, saugt die fest abgeschiedene Carbonsäure ab und löst mit Natronlauge und Salzsäure um. Das Rohprodukt fällt in sehr guter Ausbeute schon so rein (F. 223 bis 225°) an, daß es für die weiteren Zwecke meistens genügend rein ist. Aus Chlorbenzol kriställisiert es in kleinen gelben Kriställchen und schmilzt dann bei 225 bis 226°. Die Säure löst sich in wäßrigen verdünnten Alkalien mit gelber Farbe. In konzentrierter Schwefelsäure löst sich die Pyrenoyl-o-benzoesäure erst mit roter Farbe, die aber schon nach ganz kurzer Zeit nach Blau umschlägt. Beispiel e 41 Gewichtsteile Pyren, 45 Gewichtsteile 3 # 6-Dichlorphthalsäureanhydrid werden in 25o Gewichtsteilen Chlorbenzol mit 6o Gewichtsteilen Aluminiumchlorid, wie im Beispiel i angegeben ist, kondensiert. Man erhält die Pyrenoyl-3, 6-dichlor-2-benzoesäur e in ebenfalls sehr guter Ausbeute. Aus o-Dichlorbenzol kristallisiert die Säure in kleinen glänzenden gelben Kriställchen, die bei 268 bis 269° schmelzen. In konzentrierter Schwefelsäure lösen sie sich erst blaustichigrot mit sehr raschem Farbenumschlag nach Blau.Example i 72o parts by weight of pyrene are dissolved in 45o parts by weight of chlorobenzene dissolved, 525 parts by weight of phthalic anhydride were added and 1050 parts by weight of aluminum chloride gradually entered. The reaction mixture turns red-violet,: and a dark body turns out to be sandy. After all aluminum chloride entered is heated to 55 to 65 ° for 2 hours. One then carries in ice and hydrochloric acid a, blows off the chlorobenzene with steam, sucks the firmly deposited carboxylic acid and dissolves with caustic soda and hydrochloric acid. The crude product falls in very good Yield already so pure (F. 223 to 225 °) that it is mostly used for other purposes is sufficiently pure. From chlorobenzene it crystallizes in small yellow crystals and then melts at 225 to 226 °. The acid dissolves in dilute aqueous alkalis with yellow color. Pyrenoyl-o-benzoic acid dissolves in concentrated sulfuric acid at first with red color, which however changes to blue after a very short time. Example e 41 parts by weight of pyrene, 45 parts by weight of 3 # 6 dichlorophthalic anhydride are in 25o parts by weight of chlorobenzene with 6o parts by weight of aluminum chloride, as indicated in example i, condensed. Pyrenoyl-3,6-dichloro-2-benzoic acid is obtained e also in very good yield. The acid crystallizes from o-dichlorobenzene in small shiny yellow crystals that melt at 268 to 269 °. In concentrated Sulfuric acid they only dissolve bluish-tinged red with a very rapid color change to blue.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI44001D DE589145C (en) | 1932-03-15 | 1932-03-15 | Process for the preparation of pyrenoyl-o-benzoic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI44001D DE589145C (en) | 1932-03-15 | 1932-03-15 | Process for the preparation of pyrenoyl-o-benzoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE589145C true DE589145C (en) | 1933-12-02 |
Family
ID=7191167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI44001D Expired DE589145C (en) | 1932-03-15 | 1932-03-15 | Process for the preparation of pyrenoyl-o-benzoic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE589145C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2570522A (en) * | 1949-08-16 | 1951-10-09 | Petrocarbon Ltd | New pyrene condensation products and their manufacture |
-
1932
- 1932-03-15 DE DEI44001D patent/DE589145C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2570522A (en) * | 1949-08-16 | 1951-10-09 | Petrocarbon Ltd | New pyrene condensation products and their manufacture |
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