CH220965A - Process for the preparation of a lower carboxylic acid ester of tocopherol. - Google Patents
Process for the preparation of a lower carboxylic acid ester of tocopherol.Info
- Publication number
- CH220965A CH220965A CH220965DA CH220965A CH 220965 A CH220965 A CH 220965A CH 220965D A CH220965D A CH 220965DA CH 220965 A CH220965 A CH 220965A
- Authority
- CH
- Switzerland
- Prior art keywords
- tocopherol
- acid ester
- carboxylic acid
- lower carboxylic
- ester
- 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)
- Pyrane Compounds (AREA)
Description
Verfahren zur Herstellung eines niederen Carbonsäureesters des Tocopherols. d,1-Tocopherole (synthetisches Vitamin E) können durch Kondensation von Trimethyl-. hydrochinon oder Dimethylhydrochinonen mit Phytol oder Phytylhalogeniden darge stellt werden. Diese Tocopherole werden bei Einwirkung von Sauerstoff von Feuchtig keit und von Licht allmählich zerstört. Durch Veresterung werden sie haltbar.
Es wurde nun gefunden, dass niedere Car- bonsäureester der d,1-Tocopherole dadurch gewonnen werden können, dass die Konden sationsprodukte von Trimethylhydrochinon oder Dimethylhydrochinonen mit Phytol oder Phytylhalogeniden ohne vorhergehende Reinigung mit den niederen Carbonsäuren verestert und die entstehenden Ester in üb licher Weise gereinigt werden. Vorteilhafter weise erfolgt die Reinigung durch Destilla tion im Hochvakuum. Das Verfahren liefert auf kurzem und schonendem Wege sehr gute Ausbeuten.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines niederen Carbonsäureesters des Tocopherols, welches dadurch gekennzeichnet ist, dass man das rohe Kondensationsprodukt von Trimethylhydro- chinon und Phytylbromid mit einem Ben- zoylierungsmittel behandelt und den entste henden Ester reinigt. Mit Vorteil wird der Ester durch Destillation im Hochvakuum auf gearbeitet.
Der bisher unbekannte Benzoesäureester des d,1-a-Tocopherols ist ein hellgelbes, zäh flüssiges 01, welches bei 0,1 mm Druck bei 255 siedet; der Brechungsexponent n"' beträgt 1,5243. Er ist beständig und redu ziert in methylalkoholischer Lösung Silber nitrat nicht und Tollens Reagens nur all mählich. Durch Verseifung, z.
B. mit methyl- alkoholischer Kalilauge unter Luftabschluss, kann das freie Tocopherol leicht zurückge wonnen werden. Der Benzoesäureester des d,1-a-Tocopherols soll als Arzneimittel ver wendet werden. <I>Beispiel:</I> Man erhitzt ein Gemisch von 7,5 Teilen des aus Phytylbromid und Trimethylhydro- chinon erhaltenen Kondensationsproduktes mit 6 Teilen Benzoesäureanhydrid und 20 Teilen Pyridin 2 Stunden im Ölbad zum Kochen.
Nach Entfernen des Pyridins destil liert man den Rückstand im Hochvakuum. Der Benzoylester des d,1-a-Tocopherols destil liert bei 255 bei 0,1 mm.
Process for the preparation of a lower carboxylic acid ester of tocopherol. d, 1-tocopherols (synthetic vitamin E) can be obtained by condensation of trimethyl-. hydroquinone or dimethylhydroquinones with phytol or phytyl halides are Darge. These tocopherols are gradually destroyed by the action of oxygen by moisture and light. Esterification makes them durable.
It has now been found that lower carboxylic acid esters of d, 1-tocopherols can be obtained by esterifying the condensation products of trimethylhydroquinone or dimethylhydroquinones with phytol or phytyl halides without prior purification with the lower carboxylic acids and purifying the resulting esters in the usual way will. Purification is advantageously carried out by distillation in a high vacuum. The process gives very good yields in a short and gentle way.
The subject of the present patent is a process for the production of a lower carboxylic acid ester of tocopherol, which is characterized in that the crude condensation product of trimethylhydroquinone and phytyl bromide is treated with a benzoylating agent and the resulting ester is purified. The ester is advantageously worked up by distillation in a high vacuum.
The previously unknown benzoic acid ester of d, 1-a-tocopherol is a light yellow, viscous liquid oil which boils at 255 at 0.1 mm pressure; the refraction exponent n "'is 1.5243. It is stable and does not reduce silver nitrate in a methyl alcoholic solution and only gradually reduces Tollen's reagent.
B. with methyl alcoholic potassium hydroxide in the absence of air, the free tocopherol can easily be recovered. The benzoic acid ester of d, 1-a-tocopherol is said to be used as a medicinal product. <I> Example: </I> A mixture of 7.5 parts of the condensation product obtained from phytyl bromide and trimethylhydroquinone with 6 parts of benzoic anhydride and 20 parts of pyridine is heated to boiling in an oil bath for 2 hours.
After removing the pyridine, the residue is distilled in a high vacuum. The benzoyl ester of d, 1-a-tocopherol distilled at 255 at 0.1 mm.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE220965X | 1938-10-31 | ||
CH214043T | 1939-09-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH220965A true CH220965A (en) | 1942-04-30 |
Family
ID=25725538
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH220965D CH220965A (en) | 1938-10-31 | 1939-09-27 | Process for the preparation of a lower carboxylic acid ester of tocopherol. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH220965A (en) |
-
1939
- 1939-09-27 CH CH220965D patent/CH220965A/en unknown
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