DE555490C - Process for the preparation of derivatives of 1-oxo-2-alkylpropene-2 - Google Patents
Process for the preparation of derivatives of 1-oxo-2-alkylpropene-2Info
- Publication number
- DE555490C DE555490C DEI29188D DEI0029188D DE555490C DE 555490 C DE555490 C DE 555490C DE I29188 D DEI29188 D DE I29188D DE I0029188 D DEI0029188 D DE I0029188D DE 555490 C DE555490 C DE 555490C
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- aldehydes
- group
- parts
- derivatives
- 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 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001299 aldehydes Chemical class 0.000 claims description 12
- -1 aliphatic aldehydes Chemical class 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940117916 cinnamic aldehyde Drugs 0.000 description 3
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLUMOWNVWOXZAU-VQHVLOKHSA-N (e)-2-methyl-3-phenylprop-2-enal Chemical compound O=CC(/C)=C/C1=CC=CC=C1 VLUMOWNVWOXZAU-VQHVLOKHSA-N 0.000 description 2
- MOQGCGNUWBPGTQ-UHFFFAOYSA-N 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde Chemical compound CC1=C(C=O)C(C)(C)CCC1 MOQGCGNUWBPGTQ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- HEPHYCJJLAUKSB-SECBINFHSA-N (2r)-2-methyl-3-phenylpropanal Chemical compound O=C[C@H](C)CC1=CC=CC=C1 HEPHYCJJLAUKSB-SECBINFHSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N trimethylmethane Natural products CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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 Derivaten des 1-Oxo-2-alkylpropens-2 Durch das Hauptpatent 553 037 wird ein Verfahren zur Darstellung von i-Oxo-3-aryl-2-alkylpropenen-2 beansprucht, daß dadurch gekennzeichnet ist, daß man Benzaldehyd oder seine Alkylderivate mit aliphatischen Aldehyden, die mindestens vier Kohlenstoffatome enthalten und in denen eine Methylengruppe benachbart zur Oxogruppe steht, in Alkohol gelöst, in Gegenwart alkalischer Mittel und höchstens so großer Wassermen-, gen kondensiert, daß eine Störung der homogenen Phase nicht eintritt.Process for the preparation of derivatives of 1-oxo-2-alkylpropene-2 The main patent 553 037 describes a process for the preparation of i-oxo-3-aryl-2-alkylpropenen-2 claims that it is characterized in that benzaldehyde or its alkyl derivatives are used with aliphatic aldehydes containing at least four carbon atoms and in which a methylene group is adjacent to the oxo group, dissolved in alcohol, condenses in the presence of alkaline agents and at most large amounts of water, that a disturbance of the homogeneous phase does not occur.
Diese Reaktion; welche nach dem Schema m > i, verläuft, läßt sich, wie gefunden wurde, auf die Kondensation von cyclischen Aldehyden ohne CH= Gruppe in 2-Stellung zur Oxogruppe mit beliehigen aliphatischen oder araliphatischen Aldehyden, die eine CHF Gruppe in 2-Stellung zur Oxogruppe enthalten, ausdehnen, da sie auch hier bessere Ausbeuten liefert als die bekannten Verfahren.This reaction; which according to the scheme m> i, can, as has been found, be extended to the condensation of cyclic aldehydes without a CH = group in the 2-position to the oxo group with any aliphatic or araliphatic aldehydes which contain a CHF group in the 2-position to the oxo group, because here too it gives better yields than the known processes.
Zwar hat H a c k h o f e r (Monatshefte für Chemie, Bd.22 [igoi], S.98 bis 99) Benzaldehyd mit Propionaldehyd in Gegenwart von Alkohol und Kaliumhydroxyd zu i-Oxo-2-methyl-3-phenylpropen-2 (a-Methylzimtaldehyd) kondensiert, doch vollzieht sich nach seiner Arbeitsweise die Reaktion wenig glatt. Es trennt sich eine wäßrige Lösung ab, in der das Kaliumhydroxyd sich angereichert vorfindet. Dieser Umstand, vereint mit der stark erhöhten Temperatur, befördert die Aldolbildung, die noch dadurch begünstigt wird, daß die Gesamtmenge des empfindlichen Propionaldehyds von vornherein der Wirkung des Alkalis ausgesetzt wird. Durch Kondensation dieses Aldehyds mit sich selbst entstehen Verbindungen, z. B. I-Ox0-2 # 4-dimethylheptadien-2 - q. und I-0x0-a # q. # 6-trimethylnonatrien-2 - q. # 6, die einen ähnlichen Siedepunkt wie i-Oxo-2-methyl-3-phenylpropen-2 besitzen und sich von ihm nicht trennen lassen. Bei der vorliegenden Arbeitsweise wird der empfindliche Aldehyd langsam eingetropft. Es befinden sich mithin stets nur kleine Mengen des empfindlichen Aldehyds gegenüber großen Mengen des gegen Alkali weniger empfindlichen Aldehyds. Der zugetropfte Aldehyd wird aus diesem Grunde schnell mit dem im Überschuß vorgelegten Aldehyd kondensiert. Eine Schichtenbildung, wie bei H a c k h o f e r , tritt nicht ein, die Reaktion vollzieht sich daher in homögener Phase. Auch wird die heftige Erwärmung, die Hackhofers Versuchsanordnung hervorruft. welcher Umstand ebenfalls Aldolbildung und Verharzung begünstigt, durch die vorliegende Arbeitsweise völlig vermieden. Auf den Reaktionsbedingungen des beanspruchten Verfahrens beruhen die mit ihm erzielten guten Ausbeuten.It is true that H a c k h o f e r (monthly journals for chemistry, vol. 22 [igoi], Pages 98 to 99) Benzaldehyde with propionaldehyde in the presence of alcohol and potassium hydroxide condenses to i-oxo-2-methyl-3-phenylpropen-2 (a-methylcinnamaldehyde), but takes place According to his mode of operation, the reaction is not very smooth. An aqueous one separates Solution in which the potassium hydroxide is found enriched. This condition, combined with the greatly increased temperature, the aldol formation promotes, which is still is favored by the fact that the total amount of the sensitive propionaldehyde of is exposed to the action of the alkali from the outset. By condensation of this aldehyde connections arise with oneself, e.g. B. I-Ox0-2 # 4-dimethylheptadiene-2 - q. and I-0x0-a # q. # 6-trimethylnonatriene-2 - q. # 6 that have a similar boiling point like i-Oxo-2-methyl-3-phenylpropen-2 and cannot be separated from it. at In the present procedure, the sensitive aldehyde is slowly added dropwise. There are therefore always only small amounts of the sensitive aldehyde large amounts of the aldehyde, which is less sensitive to alkali. The aldehyde added dropwise is for this reason quickly condensed with the excess aldehyde. Stratification, as in H a c k h o f e r, does not occur, the reaction therefore takes place in a homogeneous phase. Also the violent warming, the Hackhofers Experimental arrangement causes. which circumstance also aldol formation and resinification favored, completely avoided by the present way of working. On the reaction conditions of the claimed process are based on the good yields achieved with it.
Bei der Kondensation mit aliphatischen oder araliphatischenAl:dehyden kann man, wie weiter gefunden wurde, im beschriebenen Verfahren die aromatischen Aldehyde durch beliebige andere Aldehyde ersetzen, die in 2-Stellung zur Oxogruppe keine CH,-Gruppe enthalten und aus diesem Grunde bei der Berührung mit alkalischen Mitteln nur schwierig mit sich selbst eineKandensation eingehen, wobei die Kondensation von aliphatischen Aldehyden mit aliphatischen Aldehyden ausgenommen wird. Das obige Reaktionsschema ist mithin umzuwandeln, in Beispiel i Man mischt 25o Teile Benzaldehyd mit einer Lösung von 15 Teilen Kaliumhydroxyd in 38o Teilen trockenem Äthylalkohol und tropft innerhalb 5 Stunden bei io° ioo Teile i-Oxopropan (Propionaldehyd) zu. Aus der homogenen Reaktionsmasse erhält man nach Entfernung des Kondensationsmittels und des Alkohols bei der Destillation im Vakuum 216 Teile i-Oxo-2-methyl-3-phenylpropen-2 (u-Methylzimtaldehyd), also mit einer Ausbeute von 86 °l, der Theorie, bezogen auf Propionaldehyd, und von 81 °P" bezogen auf den verbrauchten Benzaldehyd. Beispiel e Man mischt 33 Teile i-Oxo-3-phenylpropen-2 (Zimtaldehyd) mit einer Lösung von 13 Teilen Kaliumhydroxyd in 65o Teilen Äthylalkohol und läßt eine Mischung von 300 Teilen i-Oxo-3-phenylpropen-2 mit ioo Teilen i-Oxobutan (n-Butyraldehyd) innerhalb 5 Stunden bei io bis i2° eintropfen. Bei der Aufarbeitung der homogenen Lösung gemäß den vorigen Beispielen erhält man 233 Teile i-Oxo-2-äthyl-5-phenylpentadien-2 # 4. als gelbe, unter 12 mm Druck bei 172 bis iSo° siedende Flüssigkeit.In the case of condensation with aliphatic or araliphatic Al: dehydes, as was further found, in the process described the aromatic aldehydes can be replaced by any other aldehydes which do not contain a CH, group in the 2-position to the oxo group and, for this reason, when in contact with alkaline agents are difficult to undergo candensation with themselves, with the exception of the condensation of aliphatic aldehydes with aliphatic aldehydes. The above reaction scheme should therefore be converted into EXAMPLE 1 250 parts of benzaldehyde are mixed with a solution of 15 parts of potassium hydroxide in 38o parts of dry ethyl alcohol and i-oxopropane (propionaldehyde) is added dropwise over 5 hours at 100 parts. After removal of the condensing agent and the alcohol, 216 parts of i-oxo-2-methyl-3-phenylpropen-2 (u-methylcinnamaldehyde) are obtained from the homogeneous reaction mass in the vacuum distillation, ie with a yield of 86 ° l, theoretically , based on propionaldehyde, and of 81 ° P "based on the benzaldehyde consumed. EXAMPLE e 33 parts of i-oxo-3-phenylpropen-2 (cinnamaldehyde) are mixed with a solution of 13 parts of potassium hydroxide in 65o parts of ethyl alcohol and a mixture is left of 300 parts of i-oxo-3-phenylpropen-2 with 100 parts of i-oxobutane (n-butyraldehyde) are added dropwise within 5 hours at 10 ° to 12 ° C. Working up the homogeneous solution according to the previous examples gives 233 parts of i-oxo -2-ethyl-5-phenylpentadiene-2 # 4. As a yellow liquid boiling under 12 mm pressure at 172 to iSo °.
Beispiel 3 Man mischt 3oo Teile Benzaldehy d mit einer Lösung von 25 Teilen Kaliumhydroxyd in 5oo Teilen Äthylalkohol und tropft innerhalb 4Stunden bei 10 bis 15° iooTeile i-Oxo-3-phenylpropan zu. Man verfährt weiter nach Beispiel i und erhält Zoo Teile Benzaldehyd zurück und neben io Teilen Rückstand i4o Teile i-Oxo-2-benzyl-3-phenylpropen-2 als gelbe kristallisierte Verbindung, die unter 5 mm Druck bei 205 bis 21o° siedet.EXAMPLE 3 300 parts of benzaldehyde are mixed with a solution of 25 parts of potassium hydroxide in 500 parts of ethyl alcohol and ioo parts of i-oxo-3-phenylpropane are added dropwise over 4 hours at 10 to 15 °. The procedure of Example i is followed and zoo parts of benzaldehyde are returned and, in addition to 10 parts of residue, 14o parts of i-oxo-2-benzyl-3-phenylpropene-2 are obtained as a yellow crystallized compound which boils at 205 to 210 ° under 5 mm pressure.
Beispiel 4 35o Teile i-Oxo-2-äthylhexan mischt man mit einer Lösung von 25 Teilen Kaliumhydroxyd in 5oo Teilen Äthylalkohol und tropft innerhalb 4 Stunden bei io bis 15° ioo Teile i-Oxo-3-phenylpropan ein. Man gewinnt 24o Teile i-Oxo-2-äthylhexan zurück und neben 35 Teilen Rückstand i2o Teile i-Oxo-2-benzyl-4-äthylocten-2, eine gelbe, unter 3 mm Druck bei i8o bis 185° siedende Flüssigkeit.Example 4 35o parts of i-oxo-2-ethylhexane are mixed with a solution of 25 parts of potassium hydroxide in 500 parts of ethyl alcohol and added dropwise within 4 hours at 10 to 15 ° 100 parts of i-oxo-3-phenylpropane. 24o parts of i-oxo-2-ethylhexane are obtained back and next to 35 parts of residue i2o parts of i-oxo-2-benzyl-4-äthylocten-2, a yellow liquid boiling under 3 mm pressure at 180 to 185 °.
In ähnlicher Weise verläuft die Kondensation anderer Aldehyde. So gewinnt man z. B.The condensation of other aldehydes proceeds in a similar way. So one wins z. B.
aus 1-0x0-3-phenylpropen-2 (Zimtaldehyd) und i-Oxopropan (Propionaldehyd) i-Oxo-2-methyl-5-phenylpentadien-2 # 4, schwach gelbe Kristalle vom F. 58° und vom Kpi5 178 bis i8o°; aus i-Oxo-3-phenylpropen-2 (Zimtaldehyd) und i-Oxoheptan (Önanthaldehyd) i-Oxo-2-amyl-5-phenylpentadien-2 # 4, eine gelbe, bei 203 bis 2io° unter 15 mm Druck siedende Flüssigkeit; aus i-Oxo-2-methyl-3-phenylpropen-2 (a-Methylzimtaldehyd) und i-Oxopropan (Propionaldehyd) i-Oxo-2 # 4-dim!ethyl-5-phenylpentadien-2 # 4, schwach gelbe Kristalle vom F.43° und vom Kp14 175 bis iSo°; aus i-Oxo-2-methyl-3-phenylpropen-2 (a.-Methylzimtaldehyd) und i-Oxobutan (n-Butyraldehyd) i-Oxo-2-äthyl-4-methyl-5-phenylpentadien-2 # 4, schwach gelbe Kristalle vom Kpls 185 bis igo°.from 1-0x0-3-phenylpropen-2 (cinnamaldehyde) and i-oxopropane (propionaldehyde) i-oxo-2-methyl-5-phenylpentadiene-2 # 4, pale yellow crystals with a melting point of 58 ° and a Kpi5 178 to 18o °; from i-oxo-3-phenylpropen-2 (cinnamaldehyde) and i-oxoheptane (enanthaldehyde) i-oxo-2-amyl-5-phenylpentadiene-2 # 4, a yellow liquid boiling at 203 to 20 ° under 15 mm pressure ; from i-oxo-2-methyl-3-phenylpropen-2 (a-methylcinnamaldehyde) and i-oxopropane (propionaldehyde) i-oxo-2 # 4-dimethyl-5-phenylpentadiene-2 # 4, pale yellow crystals from F.43 ° and from Bp14 175 to iSo °; from i-oxo-2-methyl-3-phenylpropen-2 (a.-methylcinnamaldehyde) and i-oxobutane (n-butyraldehyde) i-oxo-2-ethyl-4-methyl-5-phenylpentadiene-2 # 4, weak yellow crystals from cpls 185 to igo °.
Als Aldehyde, die nach dem beanspruchten Verfahren kondensiert werden können, seien u. a. noch genannt: i-Oxobuten-2, i-Oxo- 2-methylpropan, z-Oxo-2-phenylpropan, i-0x0-3-p-tolylpropen-2, r-Oxo-2-methyl-3-phenyipropan, Cyclocitral, Furfurol.As aldehydes, which are condensed according to the claimed process can include still mentioned: i-oxobutene-2, i-oxo- 2-methylpropane, z-Oxo-2-phenylpropane, i-0x0-3-p-tolylpropen-2, r-Oxo-2-methyl-3-phenylpropane, cyclocitral, Furfural.
Als Lösungsmittel verwendet man außer Äthylalkohol andere Alkohole, z. B. Methylalkohol oder Butylalkohol.In addition to ethyl alcohol, other alcohols are used as solvents, z. B. methyl alcohol or butyl alcohol.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI29188D DE555490C (en) | 1926-10-06 | 1926-10-06 | Process for the preparation of derivatives of 1-oxo-2-alkylpropene-2 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI29188D DE555490C (en) | 1926-10-06 | 1926-10-06 | Process for the preparation of derivatives of 1-oxo-2-alkylpropene-2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE555490C true DE555490C (en) | 1932-07-29 |
Family
ID=7187244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI29188D Expired DE555490C (en) | 1926-10-06 | 1926-10-06 | Process for the preparation of derivatives of 1-oxo-2-alkylpropene-2 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE555490C (en) |
-
1926
- 1926-10-06 DE DEI29188D patent/DE555490C/en not_active Expired
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