DE1186053B - Process for the preparation of adducts from 5, 5-dialkoxy-1, 2, 3, 4-tetrachlorocyclopentadienes - Google Patents
Process for the preparation of adducts from 5, 5-dialkoxy-1, 2, 3, 4-tetrachlorocyclopentadienesInfo
- Publication number
- DE1186053B DE1186053B DEC26324A DEC0026324A DE1186053B DE 1186053 B DE1186053 B DE 1186053B DE C26324 A DEC26324 A DE C26324A DE C0026324 A DEC0026324 A DE C0026324A DE 1186053 B DE1186053 B DE 1186053B
- Authority
- DE
- Germany
- Prior art keywords
- dialkoxy
- tetrachlorocyclopentadienes
- adducts
- preparation
- chem
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- UHSMEJQTFMHABA-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,5-dimethoxycyclopenta-1,3-diene Chemical compound COC1(OC)C(Cl)=C(Cl)C(Cl)=C1Cl UHSMEJQTFMHABA-UHFFFAOYSA-N 0.000 description 2
- FEXPLBGUHRVUIU-UHFFFAOYSA-N 1,2,3,4-tetrachloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C(=O)C2=C1 FEXPLBGUHRVUIU-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- -1 anthraquinone compounds Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- UWUYOGGHJOGTMK-UHFFFAOYSA-N ClC1(C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)(Cl)Cl)Cl Chemical compound ClC1(C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)(Cl)Cl)Cl UWUYOGGHJOGTMK-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Addukten aus 5,5-Dialkoxy- 1 2,3,4-tetrachlorcyclopentadienen Die vorliegende Erfindung betrifft die Herstellung wertvoller Addukte aus 5,5-Dialkoxy-1,2,3,4-tetrachlorcyclopentadienen der allgemeinen Formel worin R einen vorzugsweise niederen Alkylrest bedeutet und der Benzol kern A noch substituiert sein kann.Process for the preparation of adducts from 5,5-dialkoxy-1,2,3,4-tetrachlorocyclopentadienes The present invention relates to the preparation of valuable adducts from 5,5-dialkoxy-1,2,3,4-tetrachlorocyclopentadienes of the general formula where R is a preferably lower alkyl radical and the benzene nucleus A can still be substituted.
Zu diesen Verbindungen gelangt man. wenn man äquimolekulare Mengen von l,4-Naphthochinon und eines 5,5-Dialkoxy-l ,2,3,4-tetrachlorcyclopentadiens der allgemeinen Formel worin R die vorstehende Bedeutung besitzt, nach an sich bekannten Verfahren auf Temperaturen oberhalb IOOGC erhitzt.One arrives at these connections. if you have equimolecular amounts of 1,4-naphthoquinone and a 5,5-dialkoxy-1,2,3,4-tetrachlorocyclopentadiene of the general formula where R has the above meaning, heated to temperatures above IOOGC by processes known per se.
Das Dialkoxytetrachlorcyclopentadien der vorstehenden allgemeinen Formel kann durch Behandeln von Hexachlorcyclopentadien. welches ein technisches Großprodukt darstellt, mit alkoholischer, beispielsweise methyl- oder äthylalkoholischer Kalilauge leicht erhalten werden. The dialkoxytetrachlorocyclopentadiene of the above general Formula can be made by treating hexachlorocyclopentadiene. which a technical Large product represents, with alcoholic, for example methyl or ethyl alcoholic Potash can easily be obtained.
Die Additionsreaktion ist exotherm und gibt, wenn sie angelaufen ist, eine beträchtliche Wärmemenge ab. Es kann sich daher bei größeren Ansätzen als zweckmäßig erweisen. die Reaktion in einem inerten Verdünnungsmittel, beispielsweise einem hochsiedenden organischen Lösungsmittel. wie Nitrobenzol, Di- oder Trichlorbenzol oder Wasser, durchzuführen. The addition reaction is exothermic and gives when started dissipates a considerable amount of heat. It can therefore apply to larger approaches Prove to be appropriate. the reaction in an inert diluent, for example a high-boiling organic solvent. such as nitrobenzene, di- or trichlorobenzene or water.
Das Reaktionsprodukt wird in kristallinem Zustand in praktisch quantitativer Ausbeute und in hoher Reinheit erhalten. Es stellt eine wertvolle Verbindung dar, die beispielsweise zur Schädlingsbekämpfung verwendet werden kann, oder vor allem als Ausgangsstoff zur Herstellung von Anthrachinonverbindungen von großem Interesse ist. So läßt es sich beispielsweise durch Behandeln mit Schwefelsäure in Tetrachlordihydroanthrachinon überführen, welch letzteres durch Behandeln mit einem Oxydationsmittel. z. B. Luftsauerstoff oder Wasserstoffperoxyd, ins Tetrachloranthrachinon übergeht. The reaction product becomes practically quantitative in the crystalline state Yield and obtained in high purity. It is a valuable connection which can be used, for example, for pest control, or above all as Starting material for the production of anthraquinone compounds of great interest is. For example, it can be converted into tetrachlorodihydroanthraquinone by treatment with sulfuric acid transfer, the latter by treating with an oxidizing agent. z. B. atmospheric oxygen or hydrogen peroxide, passes into tetrachloroanthraquinone.
Gemäß der USA.-Patentschrift 2 584 139 ist es bekannt, daß die Umsetzung des 1,4-Naphthochinons mit Hexachlorcyclopentadien nur sehr langsam und in schlechter Ausbeute. nämlich nur zu 53 bis 540in, verläuft. Ferner ist aus der Literatur (s. M c B e e, J. Am. Chem. Soc., Brd. 77. 1955. According to US Pat. No. 2,584,139, it is known that the reaction of 1,4-naphthoquinone with hexachlorocyclopentadiene only very slowly and poorly Yield. namely only to 53 to 540in. Furthermore, from the literature (s. M c B e e, J. Am. Chem. Soc., Brd. 77. 1955.
S. 285 bis 287) bekannt. daß die Reaktion des 5.5-Dimethoxy-1.2. 3,4-tetrachlorcyclopentadiens mit Benzochinon sehr langsam und unvollständig verläuft; für eine Ausbeute von 820in ist z. B. 48stündiges Erhitzen nötig.Pp. 285 to 287) known. that the reaction of 5.5-dimethoxy-1.2. 3,4-tetrachlorocyclopentadiene runs very slowly and incompletely with benzoquinone; for a yield of 820in is z. B. 48 hours of heating required.
Auf Grund dieses Standes der Technik konnte nicht mit einer derart glatten Reaktion zwischen den erfindungsgemäß zu verwendenden Komponenten gerechnet werden; der Erfolg des erfindungsgemäßen Verfahrens ist daher überraschend. Außerdem stellt das beanspruchte Verfahren eine wertvolle Bereicherung der Technik dar, da es neue technisch gangbare Wege für die Synthese von Anthrachinonverbindungen in guter Ausbeute eröffnet. Due to this state of the art could not with such a smooth reaction between the components to be used according to the invention will; the success of the process according to the invention is therefore surprising. aside from that the claimed method represents a valuable addition to the technology, since there are new technically viable routes for the synthesis of anthraquinone compounds in good yield opened.
In den nachfolgenden Beispielen bedeuten die Teile, sofern nichts anderes angegeben wird, Gewichtsteile. die Prozente Gewichtsprozente. und die Temperaturen sind in Celsiusgraden angegeben. In the examples below, the parts unless they mean nothing otherwise indicated, parts by weight. the percentages percentages by weight. and temperatures are given in degrees Celsius.
Beispiel 1 Man erhitzt eine Mischung von 158 Teilen 1.4-Naphthochinon und 264 Teilen 5.5-Dimethoxy-1,2,3,4-tetrachlorcyclopentadien auf 115 bis 1200C. Example 1 A mixture of 158 parts of 1,4-naphthoquinone is heated and 264 parts of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene at 115 to 1200C.
Bei dieser Temperatur setzt eine stark exotherme Reaktion ein, wobei vollständige Lösung eintritt.A strongly exothermic reaction sets in at this temperature, whereby complete solution occurs.
Innerhalb weniger Minuten steigt die Temperatur auf 170"C. Dann kristallisiert das Addukt unter nochmaligem Temperaturanstieg auf etwa 210° vollständig aus. Das hellgraue Reaktionsprodukt wird in praktisch quantitativer Ausbeute erhalten und ist nach einmaliger Umkristallisation aus Eisessig oder Essigsäureäthylester analysenrein; weiße Nadeln, F. 225 bis 226° (unkorrigiert).Within a few minutes the temperature rises to 170 ° C. Then crystallizes the adduct is completely exhausted while the temperature rises again to about 210 °. That light gray reaction product is obtained in practically quantitative yield and is analytically pure after single recrystallization from glacial acetic acid or ethyl acetate; white needles, F. 225 to 226 ° (uncorrected).
Wird das vorstehend erhaltene Produkt mit lO00toiger Schwefelsäure behandelt, so erfolgt unter Aufschäumen eine Abbaureaktion. bei der eine stechend riechende Substanz auftritt. Behandelt man das Abbauprodukt mit Luft oder wenig Wasserstoffperoxyd, so fällt 1.2,3,4-Tetrachloranthrachinon in gelben Nadeln an (F. 189 bis 1900, unkorrigiert. If the product obtained above is treated with 100% sulfuric acid treated, a decomposition reaction takes place with foaming. with one stabbing smelling substance occurs. If you treat the degradation product with air or a little Hydrogen peroxide, 1,2,3,4-tetrachloranthraquinone is obtained in yellow needles (F. 189 to 1900, uncorrected.
Chlorgehalt 40.9010).Chlorine content 40.9010).
Beispiel 2 63,2 Teile 1.4-Naphthochinon (=0,4Mol) und 105,6 Teile 5,5-Dimethoxy- 1.2,3,4-tetrachlorcyclopentadien (= 0,4 Mol) werden unter Rühren auf 115° erhitzt. Bei dieser Temperatur setzt eine stark exotherme Reaktion ein, wobei vollständige Lösung eintritt. Die Temperatur wird durch Zugabe von 170 Volumteilen Trichlorbenzol zwischen 150 und 1600 gehalten. Dann erwärmt man das Gemisch kurz auf 175°. läßt es auf Raumtemperatur abkühlen und rührt es bis zur vollständigen Kristallisation. Example 2 63.2 parts of 1,4-naphthoquinone (= 0.4 mol) and 105.6 parts 5,5-Dimethoxy-1,2,3,4-tetrachlorocyclopentadiene (= 0.4 mol) are added with stirring heated to 115 °. At this temperature a strongly exothermic reaction sets in, complete dissolution occurs. The temperature is increased by adding 170 parts by volume Trichlorobenzene held between 150 and 1600. Then the mixture is warmed up briefly to 175 °. let it cool to room temperature and stir it until complete Crystallization.
Das Addukt wird abfiltriert, mit Alkohol gewaschen und getrocknet. Ausbeute 147,4 Teile oder 87,30/o der Theorie. Weiße Kristalle vom Schmelzpunkt 225 (unkorrigiert), Chlorgehalt 33,60/0 (berechnet 33,600/o).The adduct is filtered off, washed with alcohol and dried. Yield 147.4 parts or 87.30 / o of theory. White crystals from the melting point 225 (uncorrected), chlorine content 33.60 / 0 (calculated 33.600 / 0).
Beispiel 3 Eine Mischung von 7,9 Teilen 1.4-Naphthochinon und 16 Teilen 5.5-Di-n-propoxy-l .2,3,4-tetrachlor- cyclopentadien wird auf 1200 erhitzt. Bei dieser Temperatur ist der Ansatz vollständig gelöst, und es beginnt ewle exotherme Reaktion, welche einen Temperaturanstieg auf etwa 1600C hervorruft. Nach kurzer Zeit fällt die Temperatur wieder, und das rohe, beigegefärbte Addukt kristallisiert in praktisch quantitativer Ausbeute aus. Es wird zur Reinigung aus Äthylalkohol umkristallisiert: weiße Kristalle vom Schmelzpunkt 174 bis 175° (unkorrigiert), Chlorgehalt 29,60wo (berechnet 29,660/0). Example 3 A mixture of 7.9 parts of 1,4-naphthoquinone and 16 Share 5.5-di-n-propoxy-l .2,3,4-tetrachloro- Cyclopentadiene is heated to 1200. At this temperature the batch is completely dissolved and an exothermic reaction begins Reaction causing the temperature to rise to around 1600C. After short After a while, the temperature falls again and the crude, beige-colored adduct crystallizes in practically quantitative yield. It is used for cleaning from ethyl alcohol recrystallized: white crystals with a melting point of 174 to 175 ° (uncorrected), Chlorine content 29.60wo (calculated 29.660 / 0).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1186053X | 1961-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1186053B true DE1186053B (en) | 1965-01-28 |
Family
ID=4561988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC26324A Pending DE1186053B (en) | 1961-02-24 | 1962-02-23 | Process for the preparation of adducts from 5, 5-dialkoxy-1, 2, 3, 4-tetrachlorocyclopentadienes |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1186053B (en) |
| NL (1) | NL275181A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1890040A (en) * | 1928-05-07 | 1932-12-06 | Gen Aniline Works Inc | Production of anthraquinone and derivatives thereof |
| US2584139A (en) * | 1947-12-27 | 1952-02-05 | Velsicol Corp | Diels-alder adducts of hexahalo-cyclopentadiene with quinones |
| DE968171C (en) * | 1954-06-02 | 1958-01-23 | Ruhrchemie Ag | Preparations for the control of harmful insects |
| DE1035651B (en) * | 1953-01-29 | 1958-08-07 | Bataafsche Petroleum | Process for the production of polycyclic pest control agents with two linearly linked bicyclo- (2, 2, 1) -heptane rings |
-
0
- NL NL275181D patent/NL275181A/xx unknown
-
1962
- 1962-02-23 DE DEC26324A patent/DE1186053B/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1890040A (en) * | 1928-05-07 | 1932-12-06 | Gen Aniline Works Inc | Production of anthraquinone and derivatives thereof |
| US2584139A (en) * | 1947-12-27 | 1952-02-05 | Velsicol Corp | Diels-alder adducts of hexahalo-cyclopentadiene with quinones |
| DE1035651B (en) * | 1953-01-29 | 1958-08-07 | Bataafsche Petroleum | Process for the production of polycyclic pest control agents with two linearly linked bicyclo- (2, 2, 1) -heptane rings |
| DE968171C (en) * | 1954-06-02 | 1958-01-23 | Ruhrchemie Ag | Preparations for the control of harmful insects |
Also Published As
| Publication number | Publication date |
|---|---|
| NL275181A (en) |
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