DE377587C - Process for the preparation of mono- and dichloro-1-ketotetrahydronaphthalene - Google Patents
Process for the preparation of mono- and dichloro-1-ketotetrahydronaphthaleneInfo
- Publication number
- DE377587C DE377587C DET25668D DET0025668D DE377587C DE 377587 C DE377587 C DE 377587C DE T25668 D DET25668 D DE T25668D DE T0025668 D DET0025668 D DE T0025668D DE 377587 C DE377587 C DE 377587C
- Authority
- DE
- Germany
- Prior art keywords
- ketotetrahydronaphthalene
- dichloro
- preparation
- mono
- chlorine
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von IViono- und Dichlor-i-ketotetrahydronaphthalin. Bei der Chlorierung aromatischer Ketone entstehen meist Gemische von Isomeren, die in der-Regel nur schwer trennbar sind- Auch gelingt es meist nicht, bei der Einführung einer bestimmten Anzahl von Chloratomen die Reaktion einheitlich zu-gestalten.Process for the preparation of IViono- and dichloro-i-ketotetrahydronaphthalene. The chlorination of aromatic ketones usually results in mixtures of isomers, the are usually difficult to separate- Also it usually does not succeed in the introduction a certain number of chlorine atoms to make the reaction uniform.
Demgegenüber wurde die Beobachtung gemacht, daß bei der Einwirkung des Chlors auf 1-Ketotetrahydronaphthalin bei Gegenwart oder Nichtgegenwart von Lösungsmitteln stets in quantitativer Ausbeute ein wohl kristallisierendes Dichlorsubstitutionsprodukt erhalten wird, das einen scharfen Schmelzpunkt von 75 bis 76° besitzt. Mäßigt man die Einwirkung des Chlors durch tiefe Tem-' peratur und weitgehende Verdünnung des i-Ketotetrahydronaphthalins mit einem organischen Lösungsmittel, so kann durch Unterbrechung der Reaktion nach Aufnahme von nur einem Molekül Chlor unschwer ein i-Ketomonochlortetrahydronaphthalin vom Schmelzpunkt 45' erhalten werden.On the other hand, it was observed that during the action of chlorine to 1-ketotetrahydronaphthalene in the presence or absence of Solvents always a well-crystallizing dichloro substitution product in quantitative yield is obtained which has a sharp melting point of 75 to 76 °. If you moderate the effect of chlorine through low temperatures and extensive dilution of the i-Ketotetrahydronaphthalins with an organic solvent, so can by interruption the reaction after the absorption of only one molecule of chlorine is easily an i-ketomonochlorotetrahydronaphthalene with a melting point of 45 '.
Beispiel 146 g r-Ketotetrahydronaphthalin werden unter Rührung mit trockenem Chlor gesättigt. Wenn die Gewichtszunahme einschließlich des in einer Wasservorlage kondensierten Chlorwasserstoffs 2 Mol. = 140 g beträgt, erstarrt das gebildete a-Ketodichlortetrahydronaphthalin in länglichen Nädelchen. Das so erhaltene Rohprodukt ist an sich schon recht rein und besitzt einen Schmelzpunkt von 72 bis 7q.°, der sich aber durch Umkristallisieren aus Eisessig oder Alkohol auf 75 bis 76° erhöhen läßt.Example 146 g of r-ketotetrahydronaphthalene are added with stirring saturated dry chlorine. If the weight gain including in a The water reserve of condensed hydrogen chloride is 2 mol. = 140 g, it solidifies formed a-ketodichlorotetrahydronaphthalene in elongated needles. The thus obtained The crude product is in itself quite pure and has a melting point of 72 to 7q. °, which, however, by recrystallization from glacial acetic acid or alcohol to 75 to 76 ° can be increased.
Zu dem gleichen Ergebnis gelangt man, wenn man die Chlorierung des 1-Ketotetrahydronaphthalins bei Gegenwart eines Lösungsmittels zur Durchführung bringt. Bei der Chlorierung von 146 g i-Ketotetrahydronaphthalin--in beispielsweise 7o g Eisessig erhält man etwa Zoo g a-Ketodichlortetrahydronaphthalin, die sich durch Filtration von der Mutterlauge leicht trennen lassen. Letztere wird alsdann als Verdünnungsmittel für eine, weitere Chlorierung verwendet.One arrives at the same result if one considers the chlorination of the 1-Ketotetrahydronaphthalins in the presence of a solvent to carry out brings. In the chlorination of 146 g of i-ketotetrahydronaphthalene - in for example 7o g of glacial acetic acid are obtained about zoo g of a-ketodichlorotetrahydronaphthalene, which is can be easily separated from the mother liquor by filtration. The latter will then used as a diluent for one more chlorination.
Beispiel 2.Example 2.
146 g 1-Ketotetrahydronaphthalin werden in 7oo g Eisessig gelöst und unter guter Kühlung mit 7o g trocknem Chlor behandelt. Beim Aufgießen auf Eis erstarrt der größte Teil des Reaktionsproduktes nach kurzer Zeit kristallinisch. Er wird von dem ölig gebliebenen Teil durch scharfes Absaugen getrennt und zeigt nach dem Umkristallisieren aus Alkohol den Schmelzpunkt 45'.146 g of 1-ketotetrahydronaphthalene are dissolved in 7oo g of glacial acetic acid and treated with 70 g dry chlorine with good cooling. Solidified when poured on ice most of the reaction product crystallized after a short time. He will separated from the oily part by sharp suction and shows after the Recrystallize from alcohol with a melting point of 45 '.
Die öligen Mutterlaugen geben bei der Weiterchlorierung nach Beispiel i reines Ketodichlortetrahydronaphthalin in quantitativer Ausbeute.The oily mother liquors give in the further chlorination according to the example i pure ketodichlorotetrahydronaphthalene in quantitative yield.
Die neuen, hier beschriebenen Produkte sollen vornehmlich als Mvttenvertilgungs- und Schädlingsbekämpfungsmittel Anwendung finden. Dannen ?ilid'sie abertauch als Zwischenprodukte bei der Herstellung von Farbstoffen, Arzneimitteln sowie in der Riechstoffindustrie verwendbar.The new products described here should primarily as a herbicide and pesticide use. Then ? ilid'sie but also as intermediate products in the manufacture of dyes and pharmaceuticals as well as usable in the fragrance industry.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET25668D DE377587C (en) | 1921-08-06 | 1921-08-06 | Process for the preparation of mono- and dichloro-1-ketotetrahydronaphthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET25668D DE377587C (en) | 1921-08-06 | 1921-08-06 | Process for the preparation of mono- and dichloro-1-ketotetrahydronaphthalene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE377587C true DE377587C (en) | 1923-06-22 |
Family
ID=7552231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET25668D Expired DE377587C (en) | 1921-08-06 | 1921-08-06 | Process for the preparation of mono- and dichloro-1-ketotetrahydronaphthalene |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE377587C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2564714A (en) * | 1948-12-29 | 1951-08-21 | Melvin S Newman | Insect repellents |
| DE1543065B1 (en) * | 1963-11-14 | 1970-12-17 | Int Flavors & Fragrances Inc | 7-acetyl-2a, 3,4,5-tetrahydro-1,1,5,5-tetramethylacenaphthene, process for its production and use as a musk fragrance |
-
1921
- 1921-08-06 DE DET25668D patent/DE377587C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2564714A (en) * | 1948-12-29 | 1951-08-21 | Melvin S Newman | Insect repellents |
| DE1543065B1 (en) * | 1963-11-14 | 1970-12-17 | Int Flavors & Fragrances Inc | 7-acetyl-2a, 3,4,5-tetrahydro-1,1,5,5-tetramethylacenaphthene, process for its production and use as a musk fragrance |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE918747C (en) | Process for the production of artificial musk fragrances from m- and p-cymene | |
| DE377587C (en) | Process for the preparation of mono- and dichloro-1-ketotetrahydronaphthalene | |
| DE888693C (en) | Process for the preparation of carbocyclic ketoximes | |
| DE933149C (en) | Process for the production of 6-methyl-ª ‡ -ionons and 6-methyl-ª ‰ -ionons | |
| DE3037487A1 (en) | METHOD FOR PRODUCING UNSATURED OR SATURATED (ALPHA), (OMEGA) DIALDEHYDES AND (ALPHA), (OMEGA) DIESEURERS | |
| DE586645C (en) | Process for the preparation of glycidic acid amides | |
| DE858701C (en) | Process for the cleavage of the lactam esters obtained in the rearrangement of oximes of cyclic ketones with sulfuric acid | |
| DE909339C (en) | Process for the preparation of homologues of butanediol- (1,4) -one- (2) | |
| DE579227C (en) | Process for the preparation of 6-methoxy-7-benzyloxy-1-methylisoquinoline | |
| DE630021C (en) | Process for the preparation of 4,5-alkyl-substituted 2-aminodiaryl ketones | |
| DE408664C (en) | Process for the preparation of decahydronaphthols | |
| DE651351C (en) | Process for the production of polynuclear, partially hydrogenated ring systems | |
| DE708114C (en) | Process for the preparation of an oxotetrahydronaphthalene | |
| DE376471C (en) | Process for the preparation of 1-chloro-2-acylaminoanthraquinones | |
| DE804566C (en) | Process for the production of butyric acid | |
| DE410099C (en) | Process for the preparation of 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone | |
| DE965321C (en) | Process for the production of pure terephthalic acid | |
| DE482438C (en) | Process for the preparation of aminoalkoxynaphthalenes | |
| DE875811C (en) | Process for the production of lactams | |
| DE626788C (en) | Process for the preparation of pure 2-acetylamino-3-chloroanthraquinone | |
| DE697268C (en) | Process for the production of straight-chain acetylene polymers in the liquid phase | |
| DE482437C (en) | Process for the preparation of 2-amino-3-oxynaphthalene | |
| DE583108C (en) | Process for the preparation of dichlorocarvacrol | |
| AT162164B (en) | Process for the preparation of α, α-di (nitrophenyl) -β, β, β-trichloroethanes. | |
| DE711018C (en) | Process for the preparation of aromatic dicarboxylic acid amides or imides |