AT58276B - Process for the preparation of fenchyl salicylate and its aliphatic acyl derivatives. - Google Patents
Process for the preparation of fenchyl salicylate and its aliphatic acyl derivatives.Info
- Publication number
- AT58276B AT58276B AT58276DA AT58276B AT 58276 B AT58276 B AT 58276B AT 58276D A AT58276D A AT 58276DA AT 58276 B AT58276 B AT 58276B
- Authority
- AT
- Austria
- Prior art keywords
- fenchyl
- salicylate
- preparation
- aliphatic acyl
- acyl derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- XQPZKMWBRDTOGK-UHFFFAOYSA-N (2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-hydroxybenzoate Chemical compound CC1(C)C(C2)CCC2(C)C1OC(=O)C1=CC=CC=C1O XQPZKMWBRDTOGK-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 14
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 8
- 229960004889 salicylic acid Drugs 0.000 description 8
- 229930006727 (-)-endo-fenchol Natural products 0.000 description 4
- IAIHUHQCLTYTSF-MRTMQBJTSA-N Fenchyl alcohol Chemical compound C1C[C@]2(C)[C@H](O)C(C)(C)[C@H]1C2 IAIHUHQCLTYTSF-MRTMQBJTSA-N 0.000 description 4
- IAIHUHQCLTYTSF-UHFFFAOYSA-N fenchyl alcohol Natural products C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- -1 salicylic acid terpene esters Chemical class 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung des Salizylsäurefenchylesters und seiner aliphatischen
Azylderivate.
Die als Antirheumatika bekannten salizylsauren Terpenester, z. B. Salizylsäurementholund Salizylsäureborneolester, haben den Nachteil, dass sie flüssig'sind und somit nur äusserlich angewendet werden können.
Es wurde nun gefunden, dass der unbekannte Salizylsäurefenchylester fest und kristallinisch, somit auch innerlich leicht dosierbar ist und z. B. den einzigen festen, salizylsauren Ester der therapeutisch verwendbaren Terpenalkohole bildet.
Die Darstellung des Salizylsäurefenchylesters erfolgt nach den üblichen Methoden.
B e i s p i e l 1: Molekulare Mengen von Salizylsäuremethylester und Fcuchylalkohol werden in einem kupfernen Gefässe unter Zusatz von Natriummethylat mehrere Stunden auf 1600 erhitzt, wobei Methyialkohol und eine kleine Menge Fenchylalkohol überdestilliert. Nach etwa sechs Stunden gibt man # Molekül Fenchylalkohol tropfenweise zu, um die Reaktion zu vervollständigen.
Die Reaktionsmasse wird in Benzol aufgenommen, mit Sodalösung bis zur neutralen Reaktion gewaschen und 1m Vakuum destilliert. Die im Vorlauf befindlichen, kleinen Mengen von Fenchyalkohol und Salizylsäuremethylester können in üblicher Weise getrennt und wiedergewonnen werden.
Beispiel 2 : Molekulare Mengen von Salizylsäure und Fenchylalkohol werden zwölf Stunden long unter Durchleitung von Kohlensäure auf 1800 erhitzt, bis kein Wasser mehr entweicht. Die Reaktionsmasse wird auf die im früheren Beispiel angegebene Weise gereinigt.
EMI1.1
und wird durch Kochen mit Sodalösung leicht verseift.
PATENT-ANSPRÜCHE :
1. Verfahren zur Darstellung des Salizylsaurefenchylesters, dadurch gekennzeichnet, dass man Fenchyla1koh01 durch Einwirkung von Salizylsaure oder ihren Alkylestern nach bekannten Methoden in Salizylsaurefenchylester überführt.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of the salicylic acid fenchyl ester and its aliphatic
Acyl derivatives.
The salicylic acid terpene esters known as antirheumatic agents, e.g. B. salicylic acid borneol and salicylic acid borneol esters have the disadvantage that they are liquid and can therefore only be used externally.
It has now been found that the unknown fenchyl salicylate is solid and crystalline, thus also easy to dose internally and z. B. forms the only solid, salicylic acid ester of the therapeutically useful terpene alcohols.
The fenchyl salicylate is prepared by the customary methods.
Example 1: Molecular amounts of methyl salicylate and fenchyl alcohol are heated to 1600 for several hours in a copper vessel with the addition of sodium methylate, with methyl alcohol and a small amount of fenchyl alcohol distilling over. After about six hours, # molecule of fenchyl alcohol is added dropwise to complete the reaction.
The reaction mass is taken up in benzene, washed with soda solution until the reaction is neutral and distilled in a vacuum. The small amounts of fenchy alcohol and salicylic acid methyl ester in the forerunner can be separated and recovered in the usual way.
Example 2: Molecular amounts of salicylic acid and fenchyl alcohol are heated to 1800 for twelve hours while passing through carbonic acid until no more water escapes. The reaction mass is purified in the manner indicated in the previous example.
EMI1.1
and is easily saponified by boiling with soda solution.
PATENT CLAIMS:
1. A process for the preparation of the salicylic acid fenchyl ester, characterized in that fenchyla1koh01 is converted into salicylic acid fenchyl ester by the action of salicylic acid or its alkyl esters by known methods.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU58276X | 1910-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT58276B true AT58276B (en) | 1913-03-26 |
Family
ID=10970797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT58276D AT58276B (en) | 1910-12-06 | 1911-11-28 | Process for the preparation of fenchyl salicylate and its aliphatic acyl derivatives. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT58276B (en) |
-
1911
- 1911-11-28 AT AT58276D patent/AT58276B/en active
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