CH175231A - Process for the preparation of 4-oxyuvitaldehyde. - Google Patents
Process for the preparation of 4-oxyuvitaldehyde.Info
- Publication number
- CH175231A CH175231A CH175231DA CH175231A CH 175231 A CH175231 A CH 175231A CH 175231D A CH175231D A CH 175231DA CH 175231 A CH175231 A CH 175231A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- oxyuvitaldehyde
- phenols
- dimethylol
- cresol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- BDLFEAFWNOROAK-UHFFFAOYSA-N 2,3-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC=C(O)C(CO)=C1CO BDLFEAFWNOROAK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- LIBWRRJGKWQFSD-UHFFFAOYSA-M sodium;2-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC=C1S([O-])(=O)=O LIBWRRJGKWQFSD-UHFFFAOYSA-M 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 4-Ogyuvitinaldehyd. Es ist bekannt, dass Isoeugenol und andere Phenole, die in Ortho- oder Par a- stellung zur Hydroxylgruppe einen Propenyl- rest enthalten, durch Oxydation ihrer Alkali salze mit Nitrobenzol in Gegenwart über schüssigen Alkalis und bei höherer Tempe ratur in die zugehörigen Aldehyde überge führt werden können (Schweiz. Patentschrift Nr. 132305).
Diese Oxydationen geschehen derart, dass die Alkalisalze der Phenole in trockenem Zustande oder bei Gegenwart von wenig Wasser bezw. konzentrierter Alkalilauge mit dein Nitrobenzol auf Temperaturen über <B>1001</B> erhitzt werden. Dabei muss man ver suchen, die mehr oder weniger heftig ver laufende Reaktion durch Rühren, durch einen grossen Cberschuss an Nitrobenzol und durch sorgfältige Beobachtung der Temperatur (Entfernung der Heizquelle bei Eintritt der Reaktion) zu mildern und gleichmässig zu gestalten.
Es wurde nun gefunden, dass alle diese Schwierigkeiten in einfachster Weise besei tigt werden können, wenn man als Oxyda tionsmittel solche Derivate aromatischer Nitrokörper verwendet, die infolge ihres Gehaltes an sauren Gruppen wasserlösliche Alkalisalze geben. Man kann dann in wäs seriger klarer Lösung die Reaktion vor sich gehen lassen, ohne zu rühren, ohne-grossen Übersehuss an Nitrokörper und ohne die Reaktion zu überwachen.
Das Verfahren kann auch angewendet werden auf Phenole, die an Stelle eines Propenylrestes in der Ortho- oder Parastellung zur Hydroxylgruppe die Carbinolgruppe enthalten, also auf Oxy- benzylalkohole. Werden die Oxybenzylalko- hole in bekannter Weise durch Kondensa tion von Formaldehyd mit Phenolen in al kalischer Lösung gewonnen,
so genügt nach- heriges Kochen des Kondensationsansatzes unter Zusatz von zum Beispiel nitrobenzol- sulfosaurem Natrium, um die Oxyaldehyde zu gewinnen.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 4-Oxy- uvitinaldehyd, welches dadurch gekennzeich net ist, dass man das Dimethylol-p-kresol der Formel:
EMI0002.0005
in wässerig-alkalischer Lösung mit Nitrover- bindungen oxydiert, die infolge ihres Gehal tes an sauren Gruppen in alkalibaltigem Wasser löslich sind und aus dem gebildeten Natriumsalz den 4-Oxyuvitinaldehyd durch Zersetzen mit Säuren gewinnt.
Beispiel: 4 Teile Dimethylol-p-kresol der oben an gegebenen Formel werden in 40 Teilen 10 %iger Natronlauge gelöst, 10 Teile m- nitrobenzolsulfosaures Natrium zugefügt und 2 Stunden im Dampfbad erhitzt. Dabei fällt das Natriumsalz des gebildeten 4-Oxyuvitin- aldehyds aus. Dasselbe wird abgesaugt und gibt beim Zersetzen mit Säuren reinen 4- Oxyuvitinaldehyd vom F.
P.<B>1330.</B> (Vergl. Berichte der Deutschen Chemischen Gesell schaft 42, 1909, Band II, Seite 2r545).
Process for the preparation of 4-ogyuvitaldehyde. It is known that isoeugenol and other phenols, which contain a propenyl radical in ortho- or par a- position to the hydroxyl group, are converted into the associated aldehydes by oxidation of their alkali salts with nitrobenzene in the presence of excess alkali and at higher temperatures can be (Swiss. Patent No. 132305).
These oxidations take place in such a way that the alkali metal salts of the phenols bezw in the dry state or in the presence of little water. concentrated alkali with your nitrobenzene to temperatures above <B> 1001 </B>. One must try to mitigate the reaction, which is more or less violent, by stirring, by using a large excess of nitrobenzene and by carefully observing the temperature (removal of the heat source when the reaction occurs) and making it uniform.
It has now been found that all of these difficulties can be eliminated in the simplest possible way if such derivatives of aromatic nitro bodies are used as oxidizing agents which give water-soluble alkali salts as a result of their content of acidic groups. The reaction can then be allowed to proceed in a clear aqueous solution without stirring, without a large excess of nitro bodies and without monitoring the reaction.
The method can also be applied to phenols which contain the carbinol group instead of a propenyl radical in the ortho or para position to the hydroxyl group, that is to say to oxybenzyl alcohols. If the oxybenzyl alcohols are obtained in a known manner by condensation of formaldehyde with phenols in an alkaline solution,
Subsequent boiling of the condensation batch with the addition of, for example, sodium nitrobenzenesulfonate is sufficient to obtain the oxyaldehydes.
The present invention relates to a process for the preparation of 4-oxy-uvitaldehyde, which is characterized in that dimethylol-p-cresol of the formula:
EMI0002.0005
oxidized in aqueous-alkaline solution with nitro compounds, which because of their acidic group content are soluble in water containing alkaline, and the 4-oxyuvitaldehyde is obtained from the sodium salt formed by decomposition with acids.
Example: 4 parts of dimethylol-p-cresol of the formula given above are dissolved in 40 parts of 10% strength sodium hydroxide solution, 10 parts of sodium m-nitrobenzenesulfonate are added and the mixture is heated in a steam bath for 2 hours. The sodium salt of the 4-oxyuvitin aldehyde formed thereby precipitates. The same is sucked off and when decomposed with acids gives pure 4-oxyuvitinaldehyde from F.
P. <B> 1330. </B> (See reports of the Deutsche Chemischen Gesellschaft 42, 1909, Volume II, page 2r545).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE175231X | 1932-05-18 | ||
| CH170080T | 1932-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH175231A true CH175231A (en) | 1935-02-15 |
Family
ID=25718833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH175231D CH175231A (en) | 1932-05-18 | 1932-12-29 | Process for the preparation of 4-oxyuvitaldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH175231A (en) |
-
1932
- 1932-12-29 CH CH175231D patent/CH175231A/en unknown
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