CH205163A - Process for the preparation of a condensation product from trimethylhydroquinone and geranyl halide. - Google Patents
Process for the preparation of a condensation product from trimethylhydroquinone and geranyl halide.Info
- Publication number
- CH205163A CH205163A CH205163DA CH205163A CH 205163 A CH205163 A CH 205163A CH 205163D A CH205163D A CH 205163DA CH 205163 A CH205163 A CH 205163A
- Authority
- CH
- Switzerland
- Prior art keywords
- trimethylhydroquinone
- preparation
- condensation product
- geranyl
- halide
- 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)
Description
Verfahren zur Darstellung eines Kondensationsproduktes aus Trimethylhydrochinon und Geranylhalogenid. Es wurde gefunden, dass bei der Einwir kung von Allylhalogeniden der allgemeinen Formel: XCH2CH=CR'R", in welcher Halogen, R' und R" Wasserstoff oder orga nische Reste bedeuten, auf Trimethylhydro- chinon in einem indifferenten Lösungsmittel in Gegenwart von Kondensationsmitteln Ver bindungen entstehen, welche den allgemeinen Formeln
EMI0001.0008
entsprechen. Wenn R' und R" Wasserstoff sind, erhält man eine Verbindung nach For mel I.
Bedeuten R' und R" organische Reste, entstehen Verbindungen nach Formel<B>11.</B> Als Kondensationsmittel können Zinkchlorid, Alu miniumchloridoderdergleichen benütztwerden.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines Konden- sationsproduktes aus Trimethylhydrochinon und Geranylhalogenid, welches dadurch ge kennzeichnet ist, dass man Geranylhalogenid auf Trimethylhydrochinon in einem indiffe renten Lösungsmittel in Gegenwart von Kon densationsmitteln einwirken lässt.
Die neue Verbindung ist ein mit Wasser dampf nicht flüchtiges Öl. Sie bildet ein Allo- phanat, welches aus farblosen Mikrokri stallen besteht, welche etwa bei 157-l58 schmelzen. Sie soll als Zwischenprodukt für die Herstellung von Arzneimitteln verwendet werden.
<I>Beispiel:</I> 10 Teile Trimethylhydrochinon werden in 600 Teilen trockenere Ligroin suspendiert. Dann setzt man 12 Teile Geranylbromid und 7,5 Teile trockenes Zinkchlorid hinzu und erhitzt die Mischung während 7-8 Stunden im Stickstoffstrom. Nach etwa 3 Stunden werden noch 3 Teile Grxeranylbromid zugege ben. Wenn die Reaktionslösung erkaltet ist, wird das Lösungsmittel im Vakuum ver dampft, der Rückstand durch Zugabe von Wasser und Äther gelöst, die Ätherschicht abgetrennt und zweimal mit verdünnter Natron lauge ausgeschüttelt.
Der nach dem Verdun sten der ätherischen Lösung verbleibende Rückstand wird mit Wasserdampf destilliert, wobei eine geringe Menge eines bräunlichen Öles übergeht. Die Hauptmenge des Reak- tionsproduktes ist mit @'Vasserdampf nicht flüchtig; sie wird durch Ausäthern zurück gewonnen und hierauf zur Reinigung in das Allophanat übergeführt.
Process for the preparation of a condensation product from trimethylhydroquinone and geranyl halide. It has been found that when allyl halides of the general formula: XCH2CH = CR'R ", in which halogen, R 'and R" are hydrogen or organic radicals, act on trimethylhydroquinone in an inert solvent in the presence of condensing agents Connections arise which correspond to the general formulas
EMI0001.0008
correspond. If R 'and R "are hydrogen, a compound according to formula I is obtained.
If R 'and R "mean organic radicals, compounds according to formula 11 are formed. Zinc chloride, aluminum chloride or the like can be used as condensing agents.
The subject of the present patent is a process for the preparation of a condensation product from trimethylhydroquinone and geranyl halide, which is characterized in that geranyl halide is allowed to act on trimethylhydroquinone in an indifferent solvent in the presence of condensation agents.
The new compound is an oil that is non-volatile with water vapor. It forms an allophanate, which consists of colorless microcrystals which melt at about 157-158. It is intended to be used as an intermediate in the manufacture of pharmaceuticals.
<I> Example: </I> 10 parts of trimethylhydroquinone are suspended in 600 parts of drier ligroin. Then 12 parts of geranyl bromide and 7.5 parts of dry zinc chloride are added and the mixture is heated in a stream of nitrogen for 7-8 hours. After about 3 hours, 3 parts of grxeranyl bromide are added. When the reaction solution has cooled down, the solvent is evaporated in vacuo, the residue is dissolved by adding water and ether, the ether layer is separated and extracted twice with dilute sodium hydroxide solution.
The residue remaining after the essential solution evaporates is distilled with steam, a small amount of a brownish oil passing over. The main part of the reaction product is not volatile with water vapor; it is recovered by etherification and then converted into the allophanate for purification.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH205163T | 1938-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205163A true CH205163A (en) | 1939-06-15 |
Family
ID=4444499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205163D CH205163A (en) | 1938-04-12 | 1938-04-12 | Process for the preparation of a condensation product from trimethylhydroquinone and geranyl halide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205163A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6006674A (en) * | 1995-11-08 | 1999-12-28 | General Electric Company | Self-steering railway truck |
-
1938
- 1938-04-12 CH CH205163D patent/CH205163A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6006674A (en) * | 1995-11-08 | 1999-12-28 | General Electric Company | Self-steering railway truck |
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