AT160293B - Process for the preparation of new oxyketones. - Google Patents
Process for the preparation of new oxyketones.Info
- Publication number
- AT160293B AT160293B AT160293DA AT160293B AT 160293 B AT160293 B AT 160293B AT 160293D A AT160293D A AT 160293DA AT 160293 B AT160293 B AT 160293B
- Authority
- AT
- Austria
- Prior art keywords
- oxyketones
- preparation
- new
- acetic acid
- diol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 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 10
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung neuer Oxyketone.
EMI1.1
*) Erstes Zusatzpatent Nr. 160291, zweites Zusatzpatent Nr. 160292.
<Desc/Clms Page number 2>
In ähnlicher Weise erhält man das 17-Äthylandrostanol-(17)-on-(3) [F=126-127 ] aus 17-Äthylandrostandiol- (3. 17) (F= 205 ] sowie das Androstanol- (17)-on- (3) JF = 182 ] aus des 3-trans- oder -cis-17-trans-Androstandiolen-(3. 17).
Beispiel 2 : 3'04g 17-Methylandrosten-(5)-diol-(3.17) [F=202-204 ] werden in 50cm3 Eisessig gelöst und mit einer Lösung von 1'6 g Brom in 10 cm Eisessig vermischt. Hierauf lässt man eine Lösung von 0'8 g Chromtrioxyd in 50 cm Eisessig hinzutropfen. Nach mehrstündigem Stehen bei Zimmertemperatur wird in Wasser gegossen, das ausgefallene Dibromid abgesaugt, gewaschen und in Eisessiglösung mit 3 g Zinkstaub umgesetzt. Die filtrierte Lösung wird in Wasser gegossen und das ausfallende 17-Methylandrosten- (4)-ol- (17)-on- (3) in Äther aufgenommen. Die gewaschene und getrocknete Ätherlösung wird eingedampft und der Rückstand aus verdünntem Alkohol bis zum konstanten Schmelzpunkt von 161-1620 umkristallisiert.
An Stelle von Eisessig kann bei der Entbromung z. B. auch Benzol als Lösungsmittel verwendet werden.
In ähnlicher Weise lässt sich, ausgehend von Androsten-(5)-diol-(3.17) [F=182-183 ] das Androsten- (4)-ol- (17)-on- (3) [F = 155 ] gewinnen.
<Desc / Clms Page number 1>
Process for the preparation of new oxyketones.
EMI1.1
*) First additional patent no.160291, second additional patent no.160292.
<Desc / Clms Page number 2>
In a similar way, 17-Ethylandrostanol- (17) -one- (3) [F = 126-127] is obtained from 17-Ethylandrostandiol- (3. 17) (F = 205] and Androstanol- (17) -one - (3) JF = 182] from des 3-trans- or -cis-17-trans-Androstandiolen- (3.17).
Example 2: 3,04 g of 17-methylandrosten- (5) -diol- (3.17) [F = 202-204] are dissolved in 50 cm3 of glacial acetic acid and mixed with a solution of 16 g of bromine in 10 cm of glacial acetic acid. A solution of 0.8 g of chromium trioxide in 50 cm of glacial acetic acid is then added dropwise. After standing for several hours at room temperature, it is poured into water, the dibromide which has precipitated is filtered off with suction, washed and reacted with 3 g of zinc dust in glacial acetic acid solution. The filtered solution is poured into water and the 17-methylandrosten- (4) -ol- (17) -one- (3) which precipitates out is taken up in ether. The washed and dried ether solution is evaporated and the residue is recrystallized from dilute alcohol to a constant melting point of 161-1620.
Instead of glacial acetic acid, z. B. benzene can also be used as a solvent.
In a similar way, starting from androstene- (5) -diol- (3.17) [F = 182-183], androstene- (4) -ol- (17) -one- (3) [F = 155] can be obtained .
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH157701X | 1935-06-18 | ||
| CH160293X | 1935-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT160293B true AT160293B (en) | 1941-04-10 |
Family
ID=29271323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT160293D AT160293B (en) | 1935-06-18 | Process for the preparation of new oxyketones. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT160293B (en) |
-
0
- AT AT160293D patent/AT160293B/en active
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