CH122241A - Process for the preparation of Bz-3-methylbenzanthrone. - Google Patents
Process for the preparation of Bz-3-methylbenzanthrone.Info
- Publication number
- CH122241A CH122241A CH122241DA CH122241A CH 122241 A CH122241 A CH 122241A CH 122241D A CH122241D A CH 122241DA CH 122241 A CH122241 A CH 122241A
- Authority
- CH
- Switzerland
- Prior art keywords
- methylbenzanthrone
- preparation
- parts
- weight
- anthrone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 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 Bz-3-Methylbenzanthron. Im Hauptpatent ist beschrieben, dass sich Anthron mit Orotonaldehyd zu Bz-3-Methyl- benzantbron kondensieren lässt, wenn in Gegenwart eines Kondensationsmittels und eines Oxydationsmittels gearbeitet wird.
Es wurde nun gefunden, dass der Zusatz von Oxydationsmitteln, wie Arsensäure, in der Schmelze nicht notwendig ist; vielmehr ge nügt die Schwefelsäure, um die bei der Kon densation sich zuerst bildenden Reduktions produkte des Bz-3-Methylbenzanthrons zu Bz-3-Methylbenzanthron zu oxydieren. Es ent steht das Produkt des Hauptpatentes mit den dort beschriebenen Eigenschaften.
<I>Beispiel</I> In ein Gemisch von 25 Gewichtsteilen Eisessig und 46 Gewichtsteilen Schwefelsäure von 73% lässt man bei 110' eine etwa 70' warme Lösung von 10 Teilen Anthron in 25 Gewichtsteilen Eisessig und 5 Gewichts- teilen Crotonaldehyd innerhalb einer Stunde eintropfen und rührt das Reaktionsgemisch bei der genannten Temperatur, bis das An thron ganz oder zum grössten Teil verschwun den ist.
Man giesst -in Wasser, saugt den Niederschlag ab und wäscht neutral.
Das Rohprodukt kann gegebenenfalls nach Behandlung mit alkalischer Hydrosulfitlösung, durch Sublimation und Umkristallisieren aus Methylalkohol gereinigt werden. Man erhält so in guter Ausbeute das in Beispiel 1 des Hauptpatentes beschriebene Bz-3-Methylbenz- anthron.
Process for the preparation of Bz-3-methylbenzanthrone. The main patent describes that anthrone can be condensed with orotonaldehyde to form Bz-3-methylbenzantbron when working in the presence of a condensing agent and an oxidizing agent.
It has now been found that the addition of oxidizing agents, such as arsenic acid, is not necessary in the melt; on the contrary, the sulfuric acid is sufficient to oxidize the reduction products of Bz-3-methylbenzanthrone which are first formed during the condensation to Bz-3-methylbenzanthrone. The product of the main patent is created with the properties described there.
<I> Example </I> In a mixture of 25 parts by weight of glacial acetic acid and 46 parts by weight of 73% sulfuric acid, an approximately 70 'warm solution of 10 parts of anthrone in 25 parts by weight of glacial acetic acid and 5 parts by weight of crotonaldehyde is left at 110' within one hour drop in and stir the reaction mixture at the temperature mentioned until the enthrone completely or for the most part has disappeared.
It is poured into water, the precipitate is filtered off and washed neutral.
The crude product can optionally be purified after treatment with alkaline hydrosulfite solution, by sublimation and recrystallization from methyl alcohol. The Bz-3-methylbenzanthrone described in Example 1 of the main patent is thus obtained in good yield.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE122241X | 1925-11-13 | ||
| CH120516T | 1925-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH122241A true CH122241A (en) | 1927-09-01 |
Family
ID=25709450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH122241D CH122241A (en) | 1925-11-13 | 1925-12-03 | Process for the preparation of Bz-3-methylbenzanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH122241A (en) |
-
1925
- 1925-12-03 CH CH122241D patent/CH122241A/en unknown
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