DE704761C - Process for the preparation of pyridine compounds - Google Patents
Process for the preparation of pyridine compoundsInfo
- Publication number
- DE704761C DE704761C DEI63979D DEI0063979D DE704761C DE 704761 C DE704761 C DE 704761C DE I63979 D DEI63979 D DE I63979D DE I0063979 D DEI0063979 D DE I0063979D DE 704761 C DE704761 C DE 704761C
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- water
- preparation
- solution
- pyridine compounds
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003222 pyridines Chemical class 0.000 title claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 6
- ZHYLFOAIESZZTR-UHFFFAOYSA-N [3-(aminomethyl)pyridin-4-yl]methanamine Chemical class NCC1=CC=NC=C1CN ZHYLFOAIESZZTR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229960003116 amyl nitrite Drugs 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 5
- -1 4,5-bisaminomethylpyridine hydrochloride Chemical compound 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 229930003270 Vitamin B Natural products 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940075930 picrate Drugs 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 235000019156 vitamin B Nutrition 0.000 description 2
- 239000011720 vitamin B Substances 0.000 description 2
- 229940011671 vitamin b6 Drugs 0.000 description 2
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical class NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical class O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- STOVUNNPUOXBQV-UHFFFAOYSA-N 5-methoxy-6-methylpyridine-3,4-dicarbonitrile Chemical compound CC1=NC=C(C(=C1OC)C#N)C#N STOVUNNPUOXBQV-UHFFFAOYSA-N 0.000 description 1
- KOGUELZXNDTWGP-UHFFFAOYSA-N 5-methoxy-6-methylpyridine-3,4-dicarboxamide Chemical compound CC1=NC=C(C(=C1OC)C(=O)N)C(=O)N KOGUELZXNDTWGP-UHFFFAOYSA-N 0.000 description 1
- DNMCXSPPDWJVAH-UHFFFAOYSA-N 5-methoxy-6-methylpyridine-3,4-dicarboxylic acid Chemical compound COC1=C(C)N=CC(C(O)=O)=C1C(O)=O DNMCXSPPDWJVAH-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- WMOFEPXAJBQESJ-UHFFFAOYSA-N [4-(aminomethyl)-5-methoxy-6-methylpyridin-3-yl]methanamine hydrochloride Chemical compound Cl.CC1=NC=C(C(=C1OC)CN)CN WMOFEPXAJBQESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung von Pyridinverbindungen Es wurde gefunden, daß man 4, 5-Bisoxymethylpyridine erhalten kann, wenn man salpetrige Säure oder salpetrige Säure abgebende Stoffe auf 4, 5-Bisaminomethylpyridine einwirken läßt. Als salpetrige Säure abgebendes Mittel wird vorzugsweise Amylnitrit verwendet. Die Abtrennung des Reaktionsproduktes kann in üblicher Weise, im besonderen auch mittels der Additionsverbindungen an Pikrinsäure o. dgl. erfolgen. plan hat schon Monoaminomethylpyridine durch Einwirken von Nitriten in saurer Lösung in die entsprechenden Monooxymethylpyridine umgewandelt (Chemisches Zentralblatt, 1936, 11, 3419,12o). Auf Grund dieser bekannten "Tatsachen konnte jedoch nicht die glatte Umwandlungsfähigkeit von 4, 5 - Bisaminomethylpyridinen in 4, 5-Bisoxymethylpyridine mittels salpetriger Säure vorausgesehen werden, da im Hinblick auf die o-Ständigkeit der beiden Aminomethylgruppen mit einem anderen Reaktionsverlauf zu rechnen war.Process for the preparation of pyridine compounds It has been found that 4,5-bisoxymethylpyridines can be obtained if nitrous acid or nitrous acid-releasing substances are allowed to act on 4,5-bisaminomethylpyridines. Amyl nitrite is preferably used as the nitrous acid releasing agent. The reaction product can be separated off in a customary manner, in particular also by means of the addition compounds with picric acid or the like. plan has already converted monoaminomethylpyridines into the corresponding monooxymethylpyridines through the action of nitrites in acidic solution (Chemisches Zentralblatt, 1936, 11, 3419,12o). On the basis of these known "facts, however, the smooth convertibility of 4,5-bisaminomethylpyridines into 4,5-bisoxymethylpyridines by means of nitrous acid could not be foreseen, since a different course of the reaction was to be expected with regard to the o-position of the two aminomethyl groups.
Die Verfahrensprodukte sollen in erster Linie zur Herstellung von Verbindungen von der Art des Vitamins B6 dienen.The process products are primarily intended for the production of Compounds of the vitamin B6 type are used.
Beispiel z 1,25 g 4, 5 - Bisaminomethylpyridinhydrochlorid werden in einer Mischung von 1 o ccm Wasser und 2o ccm Alkohol gelöst und bei Zimmertemperatur mit 1,1 ccm Amylnitrit versetzt. Nach 12 Stunden ist das Nitrit verbraucht. Es wird dann mit weiteren 5 ccm Amylnitrit versetzt und einige Zeit auf dem Wasserbad erwärmt. Dann wird unter vermindertem Druck zur Trockne eingedampft, der Rückstand in Wasser aufgenommen, mit Äther ausgeschüttelt und die wäßrige Lösung mit Pikrinsäure versetzt. Die Fällung wird abgesaugt: Nach dem Umkristallisieren erhält man gelbe Nadeln des 4., 5-Bisoxymethylpyridinpikrats, die bei 144- schmelzen. Das Pikrat wird in üblicher Weise zerlegt. Wird durch eine Lösung von 5,-, 4., 5-Bisamino- . methylpyridin F. 54- in 3o ccm Wasser bei 6o' mehrere Stunden ein Strom von Salpetrigsäureanhydrid hindurchgeleitet -und die Mischung aufgearbeitet wie oben, so erhält man dasselbe Pikrat vom Schmelzpunkt 144.'., Beispiel 2 2,9 g 2-Methyl-3-methoxy-4, 5-bisaminomethylpyridinhydrochlorid werden in einer Mischung von 2o ccm Wasser und 5o ccm Alkohol gelöst und bei Zimmertemperatur mit 1,2 g Amylnitrit versetzt. Wenn das Nitrit verbraucht ist, wird mit weiteren 5 ccm Amylnitrit versetzt und einige Zeit auf dem Wasserbad erwärmt. Dann wird die Mischung unter vermindertem Druck zur Trockne eingedampft. Der Rückstand wird in Wasser aufgenommen, die wäßrige Lösung mit Kaliumcarbonat gesättigt und mit Methylenchlorid extrahiert. Die Methylenchloridlösung wird über Kaliumcarbonat getrocknet, die Lösung filtriert und das Methylenchlorid abgedampft, Der Rückstand wird in Chloroform gelöst, die Chloroformlösung dreimal mit je 5 ccm Wasser aüsgeschütteft, die vereinigten wäßrigen Extrakte werden unter vermindertem Druck zur Trockne eingedampft, der Rückstand im Vakuum unter 4 mm Druck bei einer Heizbadtemperatur von 16o' destilliert. Man erhält ein farbloses öl, das in Methylenchlorid gelöst wird. Auf Zusatz von niedrigsiedendem Petroläther scheiden sich nach einigem Stehen im Kühlschrank farblose Kristalle ab, die, gegebenenfalls nach wiederholtem Umkristallisieren bei 89' schmelzen. Die Kristalle sind mit dem bekannten Methyläther des Vitamins B,; (Adermin) identisch. Der Mischschmelzpunkt zeigt keine Schmelzpunkterniedrigung. Das so gewonnene 2-Methyl-3-methoxy-4, 5-bisoxymethylpyridin läßt sich in bekannter Weise in das Vitamin.B,;-hydrochlorid umwandeln.Example z 1.25 g of 4,5-bisaminomethylpyridine hydrochloride are used dissolved in a mixture of 1 o cc water and 2o cc alcohol and at room temperature mixed with 1.1 cc of amyl nitrite. After 12 hours the nitrite is used up. It will then mixed with another 5 cc of amyl nitrite and warmed for some time on the water bath. It is then evaporated to dryness under reduced pressure, the residue in water taken up, extracted with ether and the aqueous solution mixed with picric acid. The precipitate is filtered off with suction: after recrystallization is obtained man yellow needles of the 4th, 5-bisoxymethylpyridine picrate melting at 144-. The picrat is disassembled in the usual way. Is produced by a solution of 5, -, 4th, 5-Bisamino- . methylpyridine F. 54- in 3o cc of water at 6o 'for several hours a stream of nitrous anhydride passed through -and the mixture worked up as above, the same thing is obtained Picrate of melting point 144. Example 2 2.9 g of 2-methyl-3-methoxy-4,5-bisaminomethylpyridine hydrochloride are dissolved in a mixture of 2o cc water and 5o cc alcohol and at room temperature mixed with 1.2 g of amyl nitrite. When the nitrite is used up, it continues with further 5 cc of amyl nitrite were added and the mixture was warmed on the water bath for some time. Then the Mixture evaporated to dryness under reduced pressure. The residue is in Added water, the aqueous solution saturated with potassium carbonate and with methylene chloride extracted. The methylene chloride solution is dried over potassium carbonate, the solution filtered and the methylene chloride evaporated, the residue is dissolved in chloroform, the chloroform solution poured out three times with 5 cc of water each time, and the combined aqueous extracts are evaporated to dryness under reduced pressure, the residue distilled in vacuo under 4 mm pressure at a heating bath temperature of 16o '. Man receives a colorless oil which is dissolved in methylene chloride. On the addition of low-boiling Petroleum ether separates colorless crystals after standing in the refrigerator for some time which, if necessary after repeated recrystallization, melt at 89 '. the Crystals are made with the well-known vitamin B methyl ether; (Adermin) identical. The mixed melting point shows no lowering of the melting point. The 2-methyl-3-methoxy-4 obtained in this way, 5-bisoxymethylpyridine can be converted into vitamin B. convert.
Das als Ausgangsstoff verwendete 2-Methyl - 3 - methoxy - ¢, 5 -bisaminomethylpyridinhydrochlorid wird durch katalytische Reduküon einer salzsauren Lösung des 2-Methyl-3-methoxy-4, 5-dicyanpyridins (Kp ",.: i io°) erhalten (vgl. Patent 702 83o), das vorerwähnte Produkt gewinnt man durch Erhitzen des 2-Methyl-3-methoxypyridin-4, 5-dicarbonsäurediamids (F. 245'' u. Zers.) mit Essigsäureanhydrid (Patent 701955). Das genannte . Dicarbonsäurediamid erhält man beim Einwirken von Ammoniak auf 2-Methyl-3 - methoxypyridin - 4. 5 - dicarbonsäuremethylester (Kp, 126'). Die zugehörige 2-Methyl-3-methoxypyridin-4, 5-dicarbonsäure wird gemäß Verfahren des Patents 702829 erhalten.The 2-methyl - 3 - methoxy - ¢, 5 -bisaminomethylpyridine hydrochloride used as starting material is obtained by catalytic reduction of a hydrochloric acid solution of 2-methyl-3-methoxy-4,5-dicyanopyridine (bp ",.: Io °) ( see patent 702 83o), the aforementioned product is obtained by heating the 2-methyl-3-methoxypyridine-4,5-dicarboxylic acid diamide (F. 245 "and decomp.) with acetic acid anhydride (patent 701955) is obtained on the action of ammonia on 2-methyl-3-methoxypyridine-4,5 -dicarboxylic acid methyl ester (bp 126 '). The associated 2-methyl-3-methoxypyridine-4,5-dicarboxylic acid is obtained according to the method of patent 702829.
Die gleiche Verbindung erhält man, wenn man 1,25g 2-Methyl-3-methoxy-4, 5-bisaminomethylpyridinhydrochlorid in i o ccm Wasser löst, die Lösung auf 6o" erwärmt und nach Zugabe einer Lösung von 4 g Natriumnitrit in 2o ccm Wasser bis zur Beendigung der Stickstoffentwicklung rührt. Nach dem Abkühlen der Mischung wird diese mit Kaliumcarbonat gesättigt und mit Methylenchlorid ausgeschüttelt. Die Methylenchloridlösung wird dreimal mit Wasser ausgeschüttelt. Aus dem wäßrigen Extrakt erhält man durch Eindampfen und Sublimieren des Rückstandes das 2-Methyl-3-methoxy-4, 5-bisoxymethylpyridin vom Schmelzpunkt 89".The same compound is obtained if 1.25 g of 2-methyl-3-methoxy-4, Dissolve 5-bisaminomethylpyridine hydrochloride in 10 cc of water and heat the solution to 60 " and after adding a solution of 4 g of sodium nitrite in 2o ccm of water to completion the evolution of nitrogen stirs. After the mixture has cooled, it is coated with potassium carbonate saturated and extracted with methylene chloride. The methylene chloride solution is shaken out three times with water. The aqueous extract is obtained by evaporation and subliming the residue the 2-methyl-3-methoxy-4,5-bisoxymethylpyridine of melting point 89 ".
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI63979D DE704761C (en) | 1939-03-04 | 1939-03-04 | Process for the preparation of pyridine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI63979D DE704761C (en) | 1939-03-04 | 1939-03-04 | Process for the preparation of pyridine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE704761C true DE704761C (en) | 1941-04-07 |
Family
ID=7196027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI63979D Expired DE704761C (en) | 1939-03-04 | 1939-03-04 | Process for the preparation of pyridine compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE704761C (en) |
-
1939
- 1939-03-04 DE DEI63979D patent/DE704761C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE704761C (en) | Process for the preparation of pyridine compounds | |
| DE863056C (en) | Process for the production of condensation products | |
| CH374071A (en) | Process for the preparation of new isoindoline derivatives | |
| DE960813C (en) | Process for the production of unsaturated ª † and ª € lactones | |
| DE662646C (en) | Process for the preparation of oxycinnamic acids | |
| DE901053C (en) | Process for the production of guanidine thiocyanate | |
| DE716579C (en) | Process for the production of ester amides of almond acid | |
| DE2558399B2 (en) | PROCESS FOR THE PREPARATION OF 3,6-DICHLOROPICOLIC ACID | |
| CH523884A (en) | Process for the production of new indole derivatives | |
| DE894994C (en) | Process for the production of aliphatic mercury ketone compounds | |
| DE2060216C3 (en) | Process for the preparation of dialkylhydroxymethylphosphine oxides | |
| DE855248C (en) | Process for the preparation of aliphatic phosphoric acid ester amides | |
| DE930686C (en) | Process for the production of dehydracetic acid | |
| DE834407C (en) | Process for the preparation of new condensation products which contain a heterocyclic ring system and a cycloaliphatic ring | |
| AT210891B (en) | Process for the production of new methylpiperidylpentanol esters | |
| DE2243112C3 (en) | Process for the preparation of substituted aromatic compounds nitrated in the side chain | |
| DE1420954C (en) | Halogen-substituted 5-phenyl-2-aminooxazolone (4) derivatives and processes for their preparation | |
| DE604920C (en) | Process for the preparation of cyclic 1,2-aminoketones | |
| DE942511C (en) | Process for the preparation of basic compounds of the monobenzo- and dibenzopyran series | |
| DE568549C (en) | Process for the preparation of 2-alkoxy-5-nitropyridines | |
| DE544893C (en) | Process for the preparation of condensation products from resorcinol and aliphatic dicarboxylic acids | |
| DE875805C (en) | Process for the preparation of the pentaerythritol dichlorohydrin monosulfuric acid ester | |
| AT33110B (en) | Process for the preparation of alkyloxyacetyl compounds of alcohols of the hydroaromatic series. | |
| AT216488B (en) | Process for the production of itaconic acid | |
| DE533038C (en) | Process for the preparation of phenylaethenyl-p-diaethoxydiphenylamidine |