CH211294A - Process for the production of a condensation product. - Google Patents
Process for the production of a condensation product.Info
- Publication number
- CH211294A CH211294A CH211294DA CH211294A CH 211294 A CH211294 A CH 211294A CH 211294D A CH211294D A CH 211294DA CH 211294 A CH211294 A CH 211294A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation product
- production
- cold
- gold chloride
- reduces
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 5
- AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- WVQQMPTVFVYDLN-QSJYAPKHSA-N (E,8S,12R)-18-hydroxy-4,8,12,16-tetramethyloctadec-16-en-2-one Chemical compound C(C)(=O)CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)=CCO WVQQMPTVFVYDLN-QSJYAPKHSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- JIGCTXHIECXYRJ-UHFFFAOYSA-N trans-phytol acetate Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)=CCOC(C)=O JIGCTXHIECXYRJ-UHFFFAOYSA-N 0.000 claims description 3
- OQVYMXCRDHDTTH-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)-2-[4-(diethoxyphosphorylmethyl)pyridin-2-yl]pyridine Chemical compound CCOP(=O)(OCC)CC1=CC=NC(C=2N=CC=C(CP(=O)(OCC)OCC)C=2)=C1 OQVYMXCRDHDTTH-UHFFFAOYSA-N 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- SUNVJLYYDZCIIK-UHFFFAOYSA-N durohydroquinone Chemical compound CC1=C(C)C(O)=C(C)C(C)=C1O SUNVJLYYDZCIIK-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 1
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- VHGBWHGICRTHIQ-UHFFFAOYSA-N phytadiene Natural products CCCCCCCCCCCCCCCC=C(/C)C=C VHGBWHGICRTHIQ-UHFFFAOYSA-N 0.000 description 1
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Kondensationsproduktes. Es ist bekannt, dass Trimethylhydrochinon mit Phytol bezw. Phy tylhalogeniden oder Phytadien zu dl-a-Tocopherol kondensiert werden kann.
Es wurde gefunden; dass ein bisher unbe kanntes Kondensationsprodukt entsteht, wenn Trimethylhydrochinon mit Acetylphytol kon densiert wird. Das gebildete Kondensations produkt kann durch Acetylierung in eine kristalline Verbindung überführt werden.
Das neue Kondensationsprodukt ist eine seifenartige Paste, löslich in Petroläther; es reduziert Kalipermanganat in der Kälte und Goldchlorid in der Wärrne. Das durch Be handlung mit Acetanhydrid daraus entstan dene Acetylderivat destilliert unter 0,08 mm Druek bei 2200 und zeigt nach Umkristalli- sieren aus Methylalkohol einen Schmelzpunkt von<B>600.</B> Es vermag Permanganat in der Kälte nicht zu reduzieren.
Durch Hydrolyse mit methylalkoholischer Schwefelsäure erhält man daraus ein Öl, welches Goldchlorid re- duziert und durch thermische Zersetzung Durohydrochinon bildet.
Das Kondensationsprodukt soll zur Her stellung von Heilmitteln mit Vitamin E-Wir- kung und als Zwischenprodukt für die Ge winnung weiterer pharmazeutisch wichtiger Verbindungen Verwendung finden. <I>Beispiel:</I> 185 Teile Aeetylphytol in 200 Teilen Benzol werden im Verlauf einer Stunde, zu einem Gemisch von 74 g Trimethylhydro- chinon in 200 cm' Benzol und 40 g wasser freiem Zinkchlorid, gelöst in 450<B>cm-'</B> trok- kenem Äther, unter Rühren bei 40 zugesetzt.
Dann wird noch 4 Stunden unter Rückfluss schwach gekocht, darauf mit Wasser versetzt und die Benzol-Ätherschicht nacheinander reit Wasser, verdünnter Salzsäure, verdünnter Natronlauge und mehrmals mit Wasser ge waschen. Nach dem Trocknen mit Natrium sulfat destilliert man die Lösungsmittel ab. Der Rückstand bildet eine seifenartige Masse. Man löst in warmem Petroläther, wobei das Kondensationsprodukt als flockiger Nieder schlag beim Erkalten ausfällt.
Die Lösung wird zentrifugiert, der Petroläther abgegossen und der Rückstand im Vakuum getrocknet. Man erhält 190 Teile einer schmierseifen- artigen Masse.
Durch Acetylieren mit 1'/E Teilen Essig säureanhydrid bei 140-1600 erhält man ein bei 220'/0,08 mm destillierendes Öl, welches aus 3 Teilen Methylalkohol umkristallisiert werden kann. Man erhält fast weisse Kristalle vom F. 60 .
Process for the production of a condensation product. It is known that trimethylhydroquinone with Phytol BEzw. Phy tylhalogeniden or phytadiene can be condensed to dl-a-tocopherol.
It was found; that a previously unknown condensation product is formed when trimethylhydroquinone is condensed with acetylphytol. The condensation product formed can be converted into a crystalline compound by acetylation.
The new condensation product is a soap-like paste, soluble in petroleum ether; it reduces potassium manganate in the cold and gold chloride in the warm. The acetyl derivative formed therefrom by treatment with acetic anhydride distills under 0.08 mm pressure at 2200 and, after recrystallization from methyl alcohol, shows a melting point of <B> 600. </B> It is unable to reduce permanganate in the cold.
By hydrolysis with methyl alcoholic sulfuric acid, an oil is obtained which reduces gold chloride and forms durohydroquinone through thermal decomposition.
The condensation product is intended to be used for the manufacture of medicinal products with vitamin E effects and as an intermediate product for the production of other pharmaceutically important compounds. <I> Example: </I> 185 parts of acetylphytol in 200 parts of benzene are converted over the course of one hour to a mixture of 74 g of trimethylhydroquinone in 200 cm 'of benzene and 40 g of anhydrous zinc chloride, dissolved in 450 cm - '</B> dry ether, added with stirring at 40.
The mixture is then gently refluxed for 4 hours, then treated with water and the benzene-ether layer is washed successively with water, dilute hydrochloric acid, dilute sodium hydroxide solution and several times with water. After drying with sodium sulfate, the solvents are distilled off. The residue forms a soap-like mass. It is dissolved in warm petroleum ether, the condensation product precipitating out as a flaky precipitate on cooling.
The solution is centrifuged, the petroleum ether is poured off and the residue is dried in vacuo. 190 parts of a soft soap-like mass are obtained.
Acetylating with 1 part of acetic anhydride at 140-1600 gives an oil which distills at 220 / 0.08 mm and which can be recrystallized from 3 parts of methyl alcohol. Almost white crystals of F. 60 are obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211294T | 1939-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211294A true CH211294A (en) | 1940-09-15 |
Family
ID=4447267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211294D CH211294A (en) | 1939-02-16 | 1939-02-16 | Process for the production of a condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211294A (en) |
-
1939
- 1939-02-16 CH CH211294D patent/CH211294A/en unknown
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