CH128127A - Process for the preparation of Bz1-oxybenzanthrone. - Google Patents
Process for the preparation of Bz1-oxybenzanthrone.Info
- Publication number
- CH128127A CH128127A CH128127DA CH128127A CH 128127 A CH128127 A CH 128127A CH 128127D A CH128127D A CH 128127DA CH 128127 A CH128127 A CH 128127A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxybenzanthrone
- preparation
- acid
- ring closure
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- FIHZWZBEAXASKA-UHFFFAOYSA-N Anthron Natural products COc1cc2Cc3cc(C)cc(O)c3C(=O)c2c(O)c1C=CC(C)C FIHZWZBEAXASKA-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- ZSFZQNSWHYVSDP-UHFFFAOYSA-G dialuminum;sodium;heptachloride Chemical compound [Na+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-] ZSFZQNSWHYVSDP-UHFFFAOYSA-G 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Bz1-Oxybenzanthron. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von Bzl- Oxybenzanthron, dadurch gekennzeichnet, dass man Anthron mit ss-Chlorpropionsäure der folgenden Formel
EMI0001.0007
kondensiert, wobei der Ringschluss unter Zu satz eines sauren Kondensationsmittels durch geführt wird.
<I>Beispiel:</I> 200 Gewichtsteile Anthron werden mit 400 Gewichtsteilen ss-Chlorpropionsäure 5 Stunden bei 130 bis<B>150'</B> gerührt, wobei Salzsäure entweicht. Nun versetzt man mit Wasser und wäscht das abgeschiedene ölige Produkt gut -aus. Durch Eindampfen der wässerigen Lösung kann die überschüssige ss-Chlorpropionsäure zurückgewonnen wer den.
Das ölig abgeschiedene Produkt wird mit verdünntem Ammoniak oder verdünnter Sada- lösung ausgezogen, filtriert und aus der nö tigenfalls mit etwas Tierkohle geklärten Lö sung die ss-Anthronylpropionsäure als helles, anfangs öliges Produkt abgeschieden.
Durch Umkristallisieren aus verdünntem Methanol oder verdünntem Eisessig erhält man dieselbe in farblosen glänzenden Na deln oder Blättchen. vom Schmelzpunkt 181 .
Die Lösung der ss-Anthronylpropionsäure in konzentrierter Schwefelsäure ist schwach gelblich. Beim Erwärmen auf ungefähr<B>150'</B> nimmt die Lösung eine rein karminrote Fär bung mit roter Fluoreszenz an. Hierbei ist Ringschluss zum Bz-Oxybenzanthron und gleichzeitig Sulfierung eingetreten.
Durch Verschmelzen der ss-Anthronyl- propionsäure mit etwa der 10fachen Menge Natriumaluminiumchlorid bei 150 bis<B>180'</B> erhält man Bzl-Oxybenzanthron. Dieses ist identisch mit dem im Patent Nr. 128125 beschriebenen Oxybenzanthron. Ebenso ge- lingt der Ringschluss @dürch Erhitzen mit Phosphoroxychlorid.
Process for the preparation of Bz1-oxybenzanthrone. The present invention relates to a process for the preparation of Bzl-oxybenzanthrone, characterized in that anthrone is mixed with β-chloropropionic acid of the following formula
EMI0001.0007
condensed, the ring closure being carried out with the addition of an acidic condensing agent.
<I> Example: </I> 200 parts by weight of anthrone are stirred with 400 parts by weight of β-chloropropionic acid for 5 hours at 130 to <B> 150 '</B>, hydrochloric acid escaping. Water is then added and the oily product which has separated out is washed thoroughly. The excess ß-chloropropionic acid can be recovered by evaporating the aqueous solution.
The oily product is extracted with dilute ammonia or dilute Sada solution, filtered and the β-anthronylpropionic acid is separated out as a pale, initially oily product from the solution, clarified with a little animal charcoal, if necessary.
Recrystallization from dilute methanol or dilute glacial acetic acid gives the same in colorless, shiny needles or flakes. from melting point 181.
The solution of ß-anthronylpropionic acid in concentrated sulfuric acid is pale yellow. When heated to about <B> 150 '</B> the solution takes on a pure carmine color with red fluorescence. Here, ring closure to the Bz-oxybenzanthrone and sulfation occurred at the same time.
Bzl-oxybenzanthrone is obtained by fusing the β-anthronyl propionic acid with approximately 10 times the amount of sodium aluminum chloride at 150 to 180 '. This is identical to the oxybenzanthrone described in Patent No. 128125. Ring closure @ is also achieved by heating with phosphorus oxychloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE128127X | 1927-03-09 | ||
| CH127266T | 1927-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH128127A true CH128127A (en) | 1928-10-01 |
Family
ID=25710843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH128127D CH128127A (en) | 1927-03-09 | 1927-04-02 | Process for the preparation of Bz1-oxybenzanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH128127A (en) |
-
1927
- 1927-04-02 CH CH128127D patent/CH128127A/en unknown
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