CH156112A - Process for the preparation of a valuable odorous substance. - Google Patents
Process for the preparation of a valuable odorous substance.Info
- Publication number
- CH156112A CH156112A CH156112DA CH156112A CH 156112 A CH156112 A CH 156112A CH 156112D A CH156112D A CH 156112DA CH 156112 A CH156112 A CH 156112A
- Authority
- CH
- Switzerland
- Prior art keywords
- valuable
- preparation
- odorous substance
- fragrance
- pressure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000126 substance Substances 0.000 title description 2
- 239000003205 fragrance Substances 0.000 claims description 7
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 239000012230 colorless oil Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BOGWRXDLEWNHCD-ZZIUEJKTSA-N citrylidene malonic acid Natural products C1C[C@@H]2[C@@H]3C[C@@]1(C)OC(=O)[C@@H]3C(=O)OC2(C)C BOGWRXDLEWNHCD-ZZIUEJKTSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- 238000011835 investigation Methods 0.000 description 1
- SPJQBGGHUDNAIC-UHFFFAOYSA-N methyl 2,5-dichlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Cl SPJQBGGHUDNAIC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines wertvollen Riechstoffes. flus den Untersuchungen von R. guhn und<B>Al.</B> Hoffer (Berliner Berichte 64, 1931, S. 1243) geht hervor, dass die durch Konden sation von Citral- und Malonsäure erhaltene sogenannte Citrylidenmalonsäure in Wirklich keit ein Dilacton der Formel I ist.
Durch Einwirkung molekularer Mengen Lauge ent- steht daraus ein Ogylacton der Formel II. Dieses gibt durch Behandeln mit einer halogen- wasserstoffhaltigen alkoholischen Lösung, z. B.
von Salzsäure in Methylalkohol, einen Dichlor- ester, den 1,4-Dihalogenmenthaii-3-essigsäure- methylester der Formel III.
EMI0001.0019
Es wurde nun gefunden, dass man zu einem wertvollen Riechstoff gelangen kann, wenn man 1,4-Dihalpgenmenthan-3-essigsäure- methylester bis zur vollständigen Abspaltung von Halogen in Form von Halogenwasserstoff erwärmt.
Der so erhaltene Riechstoff besteht ver mutlich aus einem Gemisch isomerer unge sättigter Verbindungen mit zwei Doppelbin dungen. Er bildet ein farbloses 01, das bei gewöhnlichem Druck bei 244-252 und bei 11 mm Druck bei 135-138 siedet und noch folgende durchschnittliche Konstanten zeigt:
EMI0002.0001
Der neue Riechstoff soll für Parfumerie- zwecke Verwendung äinden.
<I>Beispiel:</I> 1,4-Dichlormenthan -3-essigsäuremethyl- ester wird unter Rückfluss zum gelinden Sie den erhitzt, bis kein Chlorwasserstoff mehr entweicht. Durch Destillation des Rückstandes wird der neue Riechstoff in reinem Zustand gewonnen.
Process for the preparation of a valuable odorous substance. According to the investigations by R. Guhn and <B> Al. </B> Hoffer (Berliner Reports 64, 1931, p. 1243) it emerges that the so-called citrylidenemalonic acid obtained by the condensation of citralic and malonic acid is actually a dilactone of formula I.
The action of molecular amounts of alkali turns it into an ogylactone of the formula II. This is given by treatment with an alcoholic solution containing hydrogen halide, e.g. B.
of hydrochloric acid in methyl alcohol, a dichloro ester, the 1,4-dihalogen menthali-3-acetic acid methyl ester of the formula III.
EMI0001.0019
It has now been found that a valuable fragrance can be obtained if methyl 1,4-dihalpgene-3-acetic acid is heated until halogen is completely eliminated in the form of hydrogen halide.
The fragrance obtained in this way probably consists of a mixture of isomeric unsaturated compounds with two double bonds. It forms a colorless 01, which boils at 244-252 under normal pressure and at 135-138 under 11 mm pressure and still shows the following average constants:
EMI0002.0001
The new fragrance is intended to be used for perfumery purposes.
<I> Example: </I> 1,4-dichloromethane -3-acetic acid methyl ester is gently heated under reflux until no more hydrogen chloride escapes. The new fragrance is obtained in a pure state by distilling the residue.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH156112T | 1931-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH156112A true CH156112A (en) | 1932-07-31 |
Family
ID=4410521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH156112D CH156112A (en) | 1931-07-21 | 1931-07-21 | Process for the preparation of a valuable odorous substance. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH156112A (en) |
-
1931
- 1931-07-21 CH CH156112D patent/CH156112A/en unknown
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