CH207606A - Process for the preparation of a condensation product from B-tocopherol and allyl halide. - Google Patents
Process for the preparation of a condensation product from B-tocopherol and allyl halide.Info
- Publication number
- CH207606A CH207606A CH207606DA CH207606A CH 207606 A CH207606 A CH 207606A CH 207606D A CH207606D A CH 207606DA CH 207606 A CH207606 A CH 207606A
- Authority
- CH
- Switzerland
- Prior art keywords
- tocopherol
- condensation product
- allyl halide
- preparation
- allyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Description
Verfahren zur Herstellung eines Kondensationsproduktes ans P-Tocopherol und Allylhalogenid. Im Weizenkeimlingsöl und andern Ölen von Pflanzenkeimlingen findet sich neben dem sogenannten a-Tocopherol eine ähnliche Verbindung, die im Schrifttum unter ver schiedenen Namen, wie P-Tocopherol, Neo- tocopherol, Cumotocopherol etc. beschrieben Ist.
Es wurde nun gefunden, dass es gelingt, durch Einwirkung von a-p-ungesättigten Ha logenalkylen der Formel XCH2CR=CR'R" (X = Halogen, R, R', R" = Wasserstoff oder organische Reste) auf P-Tocopherol bei Gegenwart eines Kondensationsmittels die Alkylengruppe -CH2CR=CR'R" in ss-Toco- pherol einzuführen. Diese Alkylengruppe tritt dabei wahrscheinlich in den Benzolkern ein, und es bilden sich Homologe des ss-Toco- pherols.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines Konden sationsproduktes aus P-Tocopherol und Allyl- halogenid, welches dadurch gekennzeichnet ist, dass man Allylhalogenid in Gegenwart von Kondensationsmitteln auf P-Tocopherol einwirken lässt.
Das bisher unbekannte Kondensations produkt besitzt gegenüber Silbernitratlösung ein stärkeres Reduktionsvermögen als ss-Toco- pherol. Sein Allophanat schmilzt bei<B>1590</B> und ergab bei der Analyse folgendes Re sultat: Ber. C. 73,03 11 10,03 % Gef. C. 73,15 H 10,03 %.
Die neue Verbindung soll als Arzneimittel Verwendung finden.
<I>Beispiel:</I> 4 Teile P-Tocopherol werden in 80 Teilen trockenem Benzin vom Siedepunkt<B>70-800</B> gelöst. Dann gibt man 4 Teile wasserfreies Zinkchlorid und 20 Teile Allylbromid hinzu und erwärmt das Reaktionsgemisch zwei Stunden am Rückflusskühler zum Sieden. Während der Reaktion entweicht Bromwas- serstoff. Nach Beendigung des Umsatzes ver dünnt man mit Wasser, trennt die wässerige Schicht von der Petrolätherschicht ab, wäscht diese mit Wasser aus und dampft das Lö sungsmittel im Vakuum ab.
Es hinterbleibt ein öliger Rückstand, welcher das Konden sationsprodukt aus ss-Tocopherol und Allyl- bromid, das Allyl-p-tocopherol darstellt. Die Verbindung reduziert alkoholische Silberni tratlösung schon bei Zimmertemperatur und zeigt ein Absorptionsmaximum bei etwa 293,u,u.
Process for the production of a condensation product of P-tocopherol and allyl halide. In wheat seedling oil and other oils from plant seedlings, in addition to the so-called α-tocopherol, there is a similar compound which is described in the literature under various names, such as p-tocopherol, neotocopherol, cumotocopherol, etc.
It has now been found that it is possible, by the action of ap-unsaturated Ha logenalkylen of the formula XCH2CR = CR'R "(X = halogen, R, R ', R" = hydrogen or organic radicals) on P-tocopherol in the presence of a Condensation agent to introduce the alkylene group -CH2CR = CR'R "in ß-tocopherol. This alkylene group probably enters the benzene nucleus, and homologues of ß-tocopherol are formed.
The subject of the present patent is a process for the preparation of a condensation product from P-tocopherol and allyl halide, which is characterized in that allyl halide is allowed to act on P-tocopherol in the presence of condensing agents.
The previously unknown condensation product has a stronger reducing power than ss-tocopherol compared to silver nitrate solution. Its allophanate melts at <B> 1590 </B> and the analysis gave the following result: Ber. C. 73.03 11 10.03% found C. 73.15 H 10.03%.
The new compound is said to be used as a drug.
<I> Example: </I> 4 parts of P-tocopherol are dissolved in 80 parts of dry gasoline with a boiling point of <B> 70-800 </B>. Then 4 parts of anhydrous zinc chloride and 20 parts of allyl bromide are added and the reaction mixture is heated to boiling for two hours on a reflux condenser. Hydrogen bromide escapes during the reaction. After the conversion has ended, the mixture is diluted with water, the aqueous layer is separated from the petroleum ether layer, this is washed out with water and the solvent is evaporated off in vacuo.
What remains is an oily residue which is the condensation product of β-tocopherol and allyl bromide, the allyl-p-tocopherol. The compound reduces alcoholic silver nitride solution even at room temperature and shows an absorption maximum at about 293, u, u.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH207606T | 1938-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH207606A true CH207606A (en) | 1939-11-15 |
Family
ID=4445622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207606D CH207606A (en) | 1938-06-01 | 1938-06-01 | Process for the preparation of a condensation product from B-tocopherol and allyl halide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH207606A (en) |
-
1938
- 1938-06-01 CH CH207606D patent/CH207606A/en unknown
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