CH143246A - Process for the preparation of a compound with a hydrogenated ring system. - Google Patents
Process for the preparation of a compound with a hydrogenated ring system.Info
- Publication number
- CH143246A CH143246A CH143246DA CH143246A CH 143246 A CH143246 A CH 143246A CH 143246D A CH143246D A CH 143246DA CH 143246 A CH143246 A CH 143246A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- compound
- ring system
- hydrogenated ring
- trimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- QUVVWJCCKDPUTC-UHFFFAOYSA-N 1,6,6-trimethylcyclohex-2-ene-1-carbaldehyde Chemical compound CC1(C)CCC=CC1(C)C=O QUVVWJCCKDPUTC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/42—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with a six-membered ring
-
- 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
- C07C45/69—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 addition to carbon-to-carbon double or triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
Verfahren zur Darstellung einer Verbindung mit hydriertem Ringsystem. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Darstellung eines Trimethyl- tetrahydrobenzaldehyds, welches dadurch ge kennzeichnet ist, dass man Trimethyl-1.1.3- butadien mit Akrolein kondensiert. Die neue Verbindung soll zur Herstellung von Farb stoffen, pharmazeutischen Produkten und Riechstoffen verwendet werden. <I>Beispiel:</I> 15 (äewichtsteile Akrolein werden mit 40 Gewichtsteilen Trimethyl-1.1.3-butadien irn Druckgefäss 3 Stunden auf 100 C erhitzt.
Das Reaktionsprodukt wird bei gewöhnliehem Druck bis 120 C abdestilliert und der Rück stand dann einer Vakuumdestillation unter worfen. Das neue Produkt ist in der Frak tion Kp. 5 50 bis 100 enthalten.
Um den reinen Aldehyd zu isolieren, wird die erhaltene Rohfraktion mit der dreifachen Menge Bisulfitlauge durchgeschüttelt. Nach einigem Stehen scheidet sich die feste Bisul- fit-Doppelverbindung des Kondensationspro duktes ab. Nach dem Absaugen und Waschen mit wenig Bisulfitlauge wird die Doppelver bindung mit Sodalösung zersetzt.
Der Aldehyd scheidet sich als farbloses Öl ab; durch erneute Vakuumdestillation er hält man ihn bei Kp. 4 55 bis 57 C als farb lose Flüssigkeit von angenehmem Geruch.
Process for the preparation of a compound with a hydrogenated ring system. The subject of this additional patent is a process for the preparation of a trimethyl-tetrahydrobenzaldehyde, which is characterized in that trimethyl-1,1.3-butadiene is condensed with acrolein. The new compound is to be used in the manufacture of dyes, pharmaceutical products and fragrances. <I> Example: </I> 15 (parts by weight of acrolein are heated with 40 parts by weight of trimethyl-1.1.3-butadiene in a pressure vessel at 100 ° C. for 3 hours.
The reaction product is distilled off at normal pressure up to 120 C and the residue was then subjected to vacuum distillation. The new product is contained in the fraction Kp. 5 50 to 100.
In order to isolate the pure aldehyde, the crude fraction obtained is shaken with three times the amount of bisulfite liquor. After standing for a while, the solid bisulfite double compound of the condensation product separates out. After suctioning off and washing with a little bisulphite solution, the double connection is decomposed with soda solution.
The aldehyde separates out as a colorless oil; by renewed vacuum distillation it is kept at bp 4 55 to 57 C as a colorless liquid with a pleasant odor.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH143246T | 1928-12-10 | ||
| CH141523T | 1930-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143246A true CH143246A (en) | 1930-10-31 |
Family
ID=25713712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143246D CH143246A (en) | 1928-12-10 | 1928-12-10 | Process for the preparation of a compound with a hydrogenated ring system. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143246A (en) |
-
1928
- 1928-12-10 CH CH143246D patent/CH143246A/en unknown
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