CH123444A - Process for the preparation of an unsaturated aldehyde. - Google Patents
Process for the preparation of an unsaturated aldehyde.Info
- Publication number
- CH123444A CH123444A CH123444DA CH123444A CH 123444 A CH123444 A CH 123444A CH 123444D A CH123444D A CH 123444DA CH 123444 A CH123444 A CH 123444A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- unsaturated aldehyde
- melting point
- acid
- ethynyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims 2
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 2
- 244000246386 Mentha pulegium Species 0.000 claims description 2
- 235000016257 Mentha pulegium Nutrition 0.000 claims description 2
- 235000004357 Mentha x piperita Nutrition 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 235000001050 hortel pimenta Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WJMVPTHPBIDWHB-UHFFFAOYSA-N 2-cyclohexylideneacetaldehyde Chemical compound O=CC=C1CCCCC1 WJMVPTHPBIDWHB-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- -1 bisulfite compound Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines ungesättigten Aldehydes. Gegenstand vorliegender Erfindung ist ein Verfahren zur Darstellung eines unge sättigten Aldehydes, welches dadurch ge kennzeichnet ist, dass man 1-Äthinyl-3- methylcyclohexanol-(1) mit mindestens ein Säureradikal enthaltenden Verbindungen be handelt.
Gemäss dem Verfahren der Erfindung wird das 1-Äthinyl-3-methylcyclohexanol- (1) von der Formel
EMI0001.0008
bei der Behandlung mit Ameisensäure, Essigsäure, ,Salzsäure, Schwefelsäure, Essig säureanhydrid usw. zu einem ungesättigten Aldehyd der Formel
EMI0001.0010
das heisst zu einem Cyclohexylidenacetal- dehyd umgelagert.
Der 3 - Methylöyclohexyliden-acetaldehyd stellt ein nach einer Mischung von Pfeffer minz, Benzaldehyd und Mesityloxyd riechen des 01 dar, welches unter 10 mm Druck bei 83 bis 85 siedet und ein Semicarbazid vom Schmelzpunkt<B>203'</B> und ein Oxim vom Schmelzpunkt<B>81'</B> liefert. Die neue Verbin dung soll zur Herstellung von Riechstoffen und pharmazeutischen Präparaten oder zu andern technischen Zwecken Verwendung finden.
Beispiel 1 Gewichtsteil 1-Äthinyl-3-methylcyclo- hexanol-(1) (Siedepunkt 10 mm 76 bis <B>78',</B> Schmelzpunkt 77,5 ) wird mit 6 Vo- lumteilen technischer Ameisensäure während zirka 1 Stunde zum Sieden erhitzt. Hierauf wird die Reaktionsmasse erkalten gelassen, mit Natronlauge und Soda neutralisiert und mit Wasserdampf destilliert. Der so erhaltene Aldehyd wird durch Destillation unter ver mindertem Druck gereinigt.
Will man den Aldehyd noch weiter reinigen, so kann dies in bekannter Weise durch die Bisulfitverbin- dung, durch das Semica.rbazon, Oxim usw. geschehen.
Statt der technischen bezw. konzentrier ten Ameisensäure kann man auch verdünn- tere Ameisensäure verwenden, ebenso kann man die Reaktion auch mit andern ein Säure radikal enthaltenden Zierbindungen, zum Bei spiel Essigsäure, Schwefelsäure, Salzsäure, Dssigsäureanhy drid, ausführen.
Process for the preparation of an unsaturated aldehyde. The present invention relates to a process for the preparation of an unsaturated aldehyde, which is characterized in that 1-ethynyl-3-methylcyclohexanol- (1) is treated with compounds containing at least one acid radical.
According to the process of the invention, the 1-ethynyl-3-methylcyclohexanol- (1) is of the formula
EMI0001.0008
on treatment with formic acid, acetic acid,, hydrochloric acid, sulfuric acid, acetic anhydride, etc. to an unsaturated aldehyde of the formula
EMI0001.0010
that is, rearranged to a cyclohexylidene acetaldehyde.
3 - Methylöyclohexyliden-acetaldehyde is a smell of a mixture of peppermint, benzaldehyde and mesityloxyd, which boils at 83 to 85 under 10 mm pressure and a semicarbazide with a melting point <B> 203 '</B> and an oxime with a melting point of <B> 81 '</B>. The new connec tion is intended to be used for the production of fragrances and pharmaceutical preparations or for other technical purposes.
Example 1 Part by weight of 1-ethynyl-3-methylcyclohexanol- (1) (boiling point 10 mm 76 to 78 ', melting point 77.5) is mixed with 6 parts by volume of technical formic acid for about 1 hour Boiling heated. The reaction mass is then allowed to cool, neutralized with sodium hydroxide solution and soda and distilled with steam. The aldehyde thus obtained is purified by distillation under reduced pressure.
If one wishes to purify the aldehyde even further, this can be done in a known manner through the bisulfite compound, through the semica, rbazone, oxime, etc.
Instead of the technical or Concentrated formic acid can also be used with more dilute formic acid, and the reaction can also be carried out with other decorative bonds containing an acid, such as acetic acid, sulfuric acid, hydrochloric acid, and acetic anhydride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH121563T | 1926-03-22 | ||
| CH123444T | 1926-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH123444A true CH123444A (en) | 1927-11-16 |
Family
ID=25709705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH123444D CH123444A (en) | 1926-03-22 | 1926-03-22 | Process for the preparation of an unsaturated aldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH123444A (en) |
-
1926
- 1926-03-22 CH CH123444D patent/CH123444A/en unknown
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