CH102196A - Process for the preparation of phlorisocapronophenone. - Google Patents
Process for the preparation of phlorisocapronophenone.Info
- Publication number
- CH102196A CH102196A CH102196DA CH102196A CH 102196 A CH102196 A CH 102196A CH 102196D A CH102196D A CH 102196DA CH 102196 A CH102196 A CH 102196A
- Authority
- CH
- Switzerland
- Prior art keywords
- phlorisocapronophenone
- preparation
- water
- ketimide
- phloroglucinol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 3
- 229960001553 phloroglucinol Drugs 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N alpha-isocaproic acid Natural products CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- -1 isocaproic acid nitrile Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung von Phlorisocapronophenono Nach demselben Verfahren, das im Haupt patent zur Herstellung von Resisocaprono- phenon beschrieben \worden ist, gelingt es, aus Phloroglucin, Isocapronsäurenitril und Halogenwasserstoff über das entsprechende Ketimid das Phlorisocapronophenon herzu stellen. Die Verbindung ist ebenfalls gegen Würmer wirksam.
<I>Beispiel:</I> Zur Darstellung werden 12,6 gr trockenes Phloroglucin, 2 gr gepulvertes wasserfreies Zinkchlorid und 10 gr Isocapronsäurenitril mit 200 cm' absolutem Äther übergossen und in die Mischung bis zur Sättigung trockener Chlorwasserstoff eingeleitet. Dann lässt man 48 Stunden stehen, wobei das Ketimidchlor- hydrat des Phlorisocapronophenons auskristal lisiert.
Man giesst die Ätherlösung von den Kristallen ab, löst letztere in Wasser und verkocht die wässerige Lösung, wobei teils in der Hitze, teils beim Erkalten das Phloriso- capronophenon ausfällt. Es ist in Wasser recht schwer löslich. Die Lösung färbt sich mit Ferrichlorid braunrot. Das Keton kristallisiert mit 1 Mol. H20, schmilzt dann bei ca. 104 , in wasserfreiem Zustand bei 122 .
Process for the preparation of phlorisocapronophenono Using the same process described in the main patent for the production of resisocapronophenone, it is possible to produce phlorisocapronophenone from phloroglucinol, isocaproic acid nitrile and hydrogen halide via the corresponding ketimide. The compound is also effective against worms.
<I> Example: </I> To illustrate, 12.6 grams of dry phloroglucinol, 2 grams of powdered anhydrous zinc chloride and 10 grams of isocapronitrile are poured with 200 cm of absolute ether and dry hydrogen chloride is introduced into the mixture until it is saturated. It is then left to stand for 48 hours, during which the ketimide chlorohydrate of phlorisocapronophenone crystallizes out.
The ether solution is poured off the crystals, the latter is dissolved in water, and the aqueous solution is boiled, the phlorisocapronophenone precipitating partly in the heat and partly on cooling. It is very sparingly soluble in water. The solution turns brownish-red with ferric chloride. The ketone crystallizes with 1 mol. H20, then melts at about 104, in the anhydrous state at 122.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH97749T | 1921-06-28 | ||
| CH102196T | 1922-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH102196A true CH102196A (en) | 1923-12-01 |
Family
ID=25705309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH102196D CH102196A (en) | 1921-06-28 | 1922-11-06 | Process for the preparation of phlorisocapronophenone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH102196A (en) |
-
1922
- 1922-11-06 CH CH102196D patent/CH102196A/en unknown
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