CH398522A - Process for the preparation of secondary alcohols with anticholesterolemic activity - Google Patents

Process for the preparation of secondary alcohols with anticholesterolemic activity

Info

Publication number
CH398522A
CH398522A CH866761A CH866761A CH398522A CH 398522 A CH398522 A CH 398522A CH 866761 A CH866761 A CH 866761A CH 866761 A CH866761 A CH 866761A CH 398522 A CH398522 A CH 398522A
Authority
CH
Switzerland
Prior art keywords
preparation
secondary alcohols
anticholesterolemic
isopropyl alcohol
activity
Prior art date
Application number
CH866761A
Other languages
German (de)
Inventor
Bertone Dr Evaristo
Original Assignee
Sir Labo Chimico Biologi
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sir Labo Chimico Biologi filed Critical Sir Labo Chimico Biologi
Priority to CH866761A priority Critical patent/CH398522A/en
Publication of CH398522A publication Critical patent/CH398522A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/24—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part polycyclic without condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/34—Monohydroxylic alcohols containing six-membered aromatic rings and other rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  
 



  Verfahren zur Herstellung von sekundären Alkoholen mit Anticholesterinämie-Wirkung
Das vorliegende Verfahren bezieht sich auf die Herstellung von sekundären Alkoholen mit Anti  cholesterlnämie-Wirkung    der allgemeinen Formel    Ri-CHOH-R2    worin   Ri    ein Diphenylylradikal darstellt, das mit Alkyl, Alkoxy, Aralkyl, Hydroxyl oder Halogen substituiert sein kann, und R2 Alkyl, Aryl, Aralkyl oder Cycloalkyl bedeuten.



   Solche Verbindungen werden durch Reduktion der entsprechenden Ketonverbindungen mit Aluminium-isopropylat in Isopropylalkohol erhalten. Die vorliegende Erfindung ermöglicht im besonderen die Herstellung von Diphenylylmethylcarbinol nach einem sehr praktischen und wirtschaftlichen Reduktionsverfahren, das auf der Reduktion von p-Phenylacetophenon mit   Aluminium-isopropylat    in Isopropylalkohol beruht.



   Die aus den erwähnten Ketonen entstehenden Verbindungen sind stabil, im allgemeinen nicht toxisch und mit ausgezeichneten therapeutischen Eigenschaften begabt. Die genannten Verbindungen sind besonders geeignet für die Herstellung von Pillen, Kapseln, Suspensionen, injizierbaren Öl-Lösungen, Suppositorien, Granulaten usw.



   Wie es sich gezeigt hat, haben diese Verbindungen, neben einem sehr guten cholentischen und cholagogen Vermögen, eine bemerkenswerte anticholesterinämische Wirkung, welche sich wesentlich als Schutz und als Stimulans des Leberparenchyms auswirkt.



   Beispiel
Herstellung von Diphenylylmethylcarbinol aus p-Phenylacetophenon
EMI1.1     
 Diphenylylmethylcarbinol
In einem mit Rührer und Kühler versehenen Destillationskolben werden einer Lösung von 2,04 g Aluminium-isopropylat (0,01 Mol) in 185 cm3 Iso  propylalkohd    äquimolekulare Mengen (1,96 g) von p-Phenylacetophenon zugefügt. Darauf wird sofort mit der Entfernung von Aceton durch sehr langsame Destillation begonnen.



   Nach einigen Stunden, wenn kein mit Alkohol gemischtes Aceton mehr übergeht, wird die Destillation fortgesetzt, um das Gesamtvolumen des Destillats auf etwa 110   cm3    zu bringen.



   Darauf wird abgekühlt. 20   cm3    Wasser werden hinzugefügt. Während weiterer 15 Minuten wird am Rückfluss erwärmt und dann filtriert.



   Der Rückstand wird in der Wärme mit verschiedenen Portionen von Isopropylalkohol   (5mal    20 cm3) extrahiert. Die Extrakte werden im Vakuum konzentriert. So werden 1,60 g Rückstand (Ausbeute   88 S ;) erhalten, der aus Hexan umkristallisiert wird.   



  Schmelzpunkt   9P950    C.



   Die Verbindung ist ein mikrokristallines weisses Pulver, löslich in Alkohol,   Äther,    Chloroform und Pflanzenölen; weniger löslich in Petroläther.



  Elementaranalyse
Für   Cl4HlgO    gefunden:   7,10%    H berechnet:   7,12%    H gefunden:   84,80%    C berechnet:   84,81%    C
Nach der spektrophotometrischen Untersuchung im Ultraviolett zeigt die Absorptionskurve von Diphenylylmethylcarbinol in Isopropylalkohol ein klares Absorptionsmaximum bei einer Wellenänge von 254 Millimikron.



   Die Übereinstimmung mit dem Beerschen Gesetz ist gut bei Konzentrationen zwischen 2 und 6 Gam  ma/cm3    mit einem Optimum zwischen 3 und 6 Gam  ma/cm3. Der Extinktionskoeffizient bei 254 Millimikron in Isopropylalkohol ist
E1cm1% = 970
Die Messungen wurden mit dem Spektrophotometer  Unicam  ausgeführt.   



  
 



  Process for the preparation of secondary alcohols with anticholesterolemic activity
The present process relates to the preparation of secondary alcohols with anti-cholesterolnemia action of the general formula Ri-CHOH-R2 where Ri is a diphenylyl radical which can be substituted by alkyl, alkoxy, aralkyl, hydroxyl or halogen, and R2 is alkyl, aryl , Aralkyl or cycloalkyl.



   Such compounds are obtained by reducing the corresponding ketone compounds with aluminum isopropylate in isopropyl alcohol. In particular, the present invention enables diphenylylmethylcarbinol to be produced by a very practical and economical reduction process based on the reduction of p-phenylacetophenone with aluminum isopropylate in isopropyl alcohol.



   The compounds resulting from the aforementioned ketones are stable, generally non-toxic and have excellent therapeutic properties. The compounds mentioned are particularly suitable for the production of pills, capsules, suspensions, injectable oil solutions, suppositories, granules, etc.



   As has been shown, these compounds have, in addition to a very good cholentic and cholagogic property, a remarkable anticholesterolemic effect, which has an essential effect as a protection and as a stimulant of the liver parenchyma.



   example
Production of diphenylylmethylcarbinol from p-phenylacetophenone
EMI1.1
 Diphenylylmethylcarbinol
In a distillation flask equipped with a stirrer and condenser, equimolecular amounts (1.96 g) of p-phenylacetophenone are added to a solution of 2.04 g of aluminum isopropoxide (0.01 mol) in 185 cm3 of isopropyl alcohol. The removal of acetone by very slow distillation is then started immediately.



   After a few hours, when no more acetone mixed with alcohol passes over, the distillation is continued in order to bring the total volume of the distillate to about 110 cm3.



   It is then cooled down. 20 cm3 of water are added. The mixture is refluxed for a further 15 minutes and then filtered.



   The residue is extracted in the warm with various portions of isopropyl alcohol (5 times 20 cm3). The extracts are concentrated in vacuo. In this way 1.60 g of residue (yield 88%) are obtained, which is recrystallized from hexane.



  Melting point 9P950 C.



   The compound is a microcrystalline white powder, soluble in alcohol, ether, chloroform and vegetable oils; less soluble in petroleum ether.



  Elemental analysis
For Cl4HlgO found: 7.10% H calculated: 7.12% H found: 84.80% C calculated: 84.81% C
According to the spectrophotometric examination in the ultraviolet, the absorption curve of diphenylylmethylcarbinol in isopropyl alcohol shows a clear absorption maximum at a wavelength of 254 millimicrons.



   The agreement with Beer’s law is good at concentrations between 2 and 6 Gam ma / cm3 with an optimum between 3 and 6 Gam ma / cm3. The extinction coefficient at 254 millimicrons in isopropyl alcohol is
E1cm1% = 970
The measurements were carried out with the Unicam spectrophotometer.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von Verbindungen der Formel Rl-CHOH-R2 worin R1 ein Diphenylylradikal darstellt, das mit Alkyl, Alkoxy, Aralkyl, Hydroxyl oder Halogen substituiert sein kann, und R2 Alkyl, Aryl, Aralkyl oder Cycloalkyl bedeuten, dadurch gekennzeichnet, dass man die entsprechende Ketonverbindung der Formel Rl-CO-R2 mit Aluminium-isopropylat in Isopropylalkohol reduziert. PATENT CLAIM Process for the preparation of compounds of the formula Rl-CHOH-R2 in which R1 is a diphenylyl radical which can be substituted by alkyl, alkoxy, aralkyl, hydroxyl or halogen, and R2 is alkyl, aryl, aralkyl or cycloalkyl, characterized in that the corresponding ketone compound of the formula Rl-CO-R2 reduced with aluminum isopropylate in isopropyl alcohol.
CH866761A 1961-07-27 1961-07-27 Process for the preparation of secondary alcohols with anticholesterolemic activity CH398522A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH866761A CH398522A (en) 1961-07-27 1961-07-27 Process for the preparation of secondary alcohols with anticholesterolemic activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH866761A CH398522A (en) 1961-07-27 1961-07-27 Process for the preparation of secondary alcohols with anticholesterolemic activity

Publications (1)

Publication Number Publication Date
CH398522A true CH398522A (en) 1966-03-15

Family

ID=4343292

Family Applications (1)

Application Number Title Priority Date Filing Date
CH866761A CH398522A (en) 1961-07-27 1961-07-27 Process for the preparation of secondary alcohols with anticholesterolemic activity

Country Status (1)

Country Link
CH (1) CH398522A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4714789A (en) * 1985-07-26 1987-12-22 P. F. Medicament Halo-biphenyl tertiary alcohols useful in therapy in the treatment of atherosclerosis

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4714789A (en) * 1985-07-26 1987-12-22 P. F. Medicament Halo-biphenyl tertiary alcohols useful in therapy in the treatment of atherosclerosis

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