CH123449A - Process for the preparation of an unsaturated aldehyde. - Google Patents
Process for the preparation of an unsaturated aldehyde.Info
- Publication number
- CH123449A CH123449A CH123449DA CH123449A CH 123449 A CH123449 A CH 123449A CH 123449D A CH123449D A CH 123449DA CH 123449 A CH123449 A CH 123449A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- unsaturated aldehyde
- acid
- semicarbazone
- 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 1
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- VZPBTNPWFOMXPI-UHFFFAOYSA-N 3,7-dimethyloct-1-yn-3-ol Chemical compound CC(C)CCCC(C)(O)C#C VZPBTNPWFOMXPI-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- -1 methyl isoheptylidene acetaldehyde Chemical compound 0.000 claims description 3
- 150000007659 semicarbazones Chemical class 0.000 claims description 3
- 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
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000012230 colorless 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
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002923 oximes Chemical class 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
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- 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)
- Fats And Perfumes (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-thinyl-methyliso-- hexylcarbinol mit mindestens ein Säureradi kal enthaltenden Verbindungen behandelt.
Gemäss dem Verfahren der vorliegenden Erfindung wird. das Äthinyl-methylisohexyl- carbinol von der Formel
EMI0001.0008
bei der Behandlung mit Ameisensäure, Essig säure, Salzsäure, Schwefelsäure, Essigsäure anhydrid usw. zu einem ungesättigten Alde hyd der Formel
EMI0001.0010
dem Methyl-isoheptyliden-acetaldehyd (Di- hydrocitral) umgelagert, welcher ein stark nach Pfefferminz und Pseudojonon riechen des, farbloses<B>01</B> darstellt, welches unter 9 mm Druck bei 85 bis 86 siedet und ein Semicarbazon vom Schmelzpunkt<B>170'</B> bil det.
Die neue Verbindung soll zur Herstel lung von Riechstoffen und pharmazeutischen Präparaten oder zu andern technischen Zwecken Verwendung finden.
Beispiel: 1 Gewichtsteil;' Äthinyl-methylisohexyl- carbinol (vergleiche Armales de Chemie 1924, Seite 8,69) wird mit 6 Volumteilen techni scher Ameisensäure während zirka; 1 Stuhde zum Sieden erhitzt. Hierauf wird die Reak tionsmasse erkalten gelassen, mit Natronlauge und Soda neutralisiert und mit Wasserdampf destilliert. Der so erhaltene Aldehyd wird durch Destillation unter vermindertem Druck gereinigt.
Will man den Aldehyd noch wei ter reinigen, so kann dies in bekannter Weise durch ,die Bisulfitverbindung, durch das Semi- carbazon, Oxim usw. geschehen.
Statt der technischen bezw. konzentrier ten Ameisensäure kann man auch verdünntere Ameisensäure verwenden, ebenso kann man die Reaktion auch mit andern ein Säureradi kal enthaltenden Verbindungen, zum Beispiel Essigsäure, Salzsäure, Schwefelsäure, Essig säureanhydrid, 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-thynyl-methyliso- hexylcarbinol is treated with compounds containing at least one acid radical.
According to the method of the present invention. the ethynyl-methylisohexyl-carbinol 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
rearranged to methyl isoheptylidene acetaldehyde (dihydrocitral), which has a strong smell of peppermint and pseudo-jonone, colorless <B> 01 </B>, which boils at 85 to 86 under 9 mm pressure and a semicarbazone with a melting point < B> 170 '</B> forms.
The new compound is intended to be used for the manufacture of fragrances and pharmaceutical preparations or for other technical purposes.
Example: 1 part by weight; ' Ethynyl-methylisohexyl-carbinol (compare Armales de Chemie 1924, page 8,69) is with 6 parts by volume of technical formic acid for about; Heated to the boil for 1 hour. 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 the aldehyde is to be purified further, this can be done in a known manner by means of the bisulfite compound, the semicarbazone, oxime, etc.
Instead of the technical or concentrated formic acid can also be used more dilute formic acid, and the reaction can also be carried out with other compounds containing an acid radical, for example acetic acid, hydrochloric acid, sulfuric acid, acetic anhydride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH121563T | 1926-03-22 | ||
| CH123449T | 1926-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH123449A true CH123449A (en) | 1927-11-16 |
Family
ID=25709710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH123449D CH123449A (en) | 1926-03-22 | 1926-03-22 | Process for the preparation of an unsaturated aldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH123449A (en) |
-
1926
- 1926-03-22 CH CH123449D patent/CH123449A/en unknown
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