DE279864C - - Google Patents
Info
- Publication number
- DE279864C DE279864C DENDAT279864D DE279864DA DE279864C DE 279864 C DE279864 C DE 279864C DE NDAT279864 D DENDAT279864 D DE NDAT279864D DE 279864D A DE279864D A DE 279864DA DE 279864 C DE279864 C DE 279864C
- Authority
- DE
- Germany
- Prior art keywords
- distilled
- vacuo
- colorless
- forms
- allyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
- 238000000034 method Methods 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- -1 hydrogen halides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Description
ffff
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Ve 279864 -KLASSE 12 o. GRUPPE Ve 279864 - CLASS 12 or GROUP
FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. CÖLN.FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. COLOGNE.
Verfahren zur Darstellung von «-Methylcumaranen. Patentiert im Deutschen Reiche vom 9. Oktober 1913 ab. Process for the preparation of -methyl coumarans. Patented in the German Empire on October 9, 1913.
In der Patentschrift 268099, Kl. 120; ist • - ein Verfahren zur Herstellung von o-Allylphenolen und ihren Analogen beschrieben.In patent specification 268099, class 120; is • - a process for the production of o-allylphenols and their analogues.
Es wurde nun gefunden, daß diese C-o-Allylphenole in a-Methylcumarane übergeführt werden können. Diese Überführung kann in der Weise bewerkstelligt werden, daß man die Allylphenole mit Halogenwasserstoff behandelt und das Reaktionsprodukt eventuell nach vor- ■x 10 hergehender Erwärmung mit alkoholischem " Alkali im Vakuum destilliert, oder daß man o-Allylphenole mit sauren Kondensationsmitteln auf höhere Temperatur erhitzt und die gebildeten α-Methylcumarane eventuell im Vakuum abdestilliert. Die neuen Körper bilden farblose Flüssigkeiten und geben mit Eisenchlorid und konzentrierter Schwefelsäure eine charakteristische rotviolette Färbung. Sie sollen für pharmazeutische Zwecke Verwendung finden. -It has now been found that these co-allylphenols can be converted into α-methylcoumarans. This conversion can be accomplished in such a way that treating the allyl phenols with hydrogen halide and the reaction product may be distilled in vacuo by full ■ x 10 reciprocating heating with alcoholic "alkali, or in that o-allylphenols heated to higher temperature with acidic condensing agents and the α-methylcoumarans formed may be distilled off in vacuo. The new bodies form colorless liquids and, with ferric chloride and concentrated sulfuric acid, give a characteristic red-violet color. They are said to be used for pharmaceutical purposes.
50 g o-Allyl-p-kresol werden ohne äußere Kühlung mit Bromwasserstoffgas gesättigt und nach mehrstündigem Stehen im Vakuum destilliert. Das Destillat wird mit Natronlauge gewaschen, in Petroläther gelöst und nach dem Trocknen der Lösung mit Kaliumkarbonat und mit wenig metallischem Natrium behandelt und unter gewöhnlichem Druck destilliert. Das so erhaltene α-3-Dimethylcumaran hat die-Formel:50 g of o-allyl-p-cresol are without external Cooling is saturated with hydrogen bromide gas and, after standing for several hours, distilled in vacuo. The distillate is washed with sodium hydroxide solution, dissolved in petroleum ether and, after the solution has been dried, with potassium carbonate and treated with a little metallic sodium and distilled under ordinary pressure. The α-3-dimethylcoumaran thus obtained has the formula:
CH3-CH2
I
XH-CH3 CH 3 -CH 2 I.
XH-CH 3
11
und bildet eine wasserhelle Flüssigkeit vom Siedepunkt 219 ° und angenehmem aromati-* sehen Geruch, die sich in den gewöhnlichen organischen Lösungsmitteln löst, dagegen in Natronlauge unlöslich ist und bei Behandlung mit metallischem Natrium sich nicht verändert. . : Beispiel 2.and forms a water-white liquid with a boiling point of 219 ° and a pleasant aromatic * see odor that dissolves in common organic solvents, on the other hand Sodium hydroxide is insoluble and does not change when treated with metallic sodium. . : Example 2.
100 Teile o-Allylphenol werden mit 10 Teilen salzsaurem Pyridin einige Zeit auf etwa*·"1'"' 220° erhitzt und sodann im Vakuum destilliert. Das Destillat wird in Äther gelöst, dann mit Mineralsäure und Natronlauge gewaschen, über Kaliumkarbonat getrocknet und unter gewöhnlichem Druck destilliert. Das erhaltene ct-Methylcumaran siedet bei 197 bis 198 ° und bildet ein farbloses, eigenartig riechendes öl, das in seinen Eigenschaften dem Produkt des Beispiels 1 gleicht.100 parts of o-allylphenol are heated with 10 parts of hydrochloric acid pyridine to about * · " 1 '"' 220 ° for some time and then distilled in vacuo. The distillate is dissolved in ether, then washed with mineral acid and sodium hydroxide solution, dried over potassium carbonate and distilled under ordinary pressure. The ct-methylcoumaran obtained boils at 197 ° to 198 ° and forms a colorless, peculiar smelling oil, the properties of which are similar to the product of Example 1.
Das nach dem gleichen Verfahren aus o-Allylo-kresol erhaltene a-i-DimethylcumaranThe same procedure from o-allylo-cresol obtained a-i-dimethylcoumaran
-CH2 I
CH-CH3 -CH 2 I.
CH-CH 3
CHa CH a
bildet eine farblose Flüssigkeit von ausgesprochenem Blumengeruch, die bei 211 bis 212° siedet; der α - Methylcumaran - 3 - carbonsäuremethylester forms a colorless liquid with a pronounced floral odor, which at 211 to Boils at 212 °; the α-methylcoumaran-3-carboxylic acid methyl ester
C2 H5OOC-C 2 H 5 OOC-
CH-CH,CH-CH,
den man nach einer der beschriebenen Methoden aus 3-Allyl-4-oxybenzoesäuremethylester erhalten kann, siedet bei 167 bis 168 ° unter einem Druck von 15 mm und bildet ein farbloses Öl von schwachem Geruch, das durch Verseifen die a-Methylcumaran-3-carbonsäure liefert, farblose Nadeln vom Schmelzpunkt ,/ 1500. „, '■*which can be obtained from 3-allyl-4-oxybenzoic acid methyl ester by one of the methods described, boils at 167 to 168 ° under a pressure of 15 mm and forms a colorless oil with a faint odor, which by saponifying the a-methylcoumaran-3-carboxylic acid yields, colorless needles with a melting point of / 150 0 . ", '■ *
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE279864C true DE279864C (en) |
Family
ID=535746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT279864D Active DE279864C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE279864C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2421812A (en) * | 1939-07-14 | 1947-06-10 | Univ Minnesota | Method of producing chroman compounds |
| US2421811A (en) * | 1939-07-14 | 1947-06-10 | Univ Minnesota | Process for producing chroman compounds |
| US2548704A (en) * | 1949-08-17 | 1951-04-10 | Dow Chemical Co | Substituted 2,3-dihydro-2-methylbenzofurans |
| US2937188A (en) * | 1951-11-15 | 1960-05-17 | Gen Aniline & Film Corp | 2-methyl 2, 3-dihydrobenzofurancarboxylic acids and acid halides |
| FR2634203A1 (en) * | 1988-07-13 | 1990-01-19 | Inst Rech Controles Techn | 2,3-Dihydrobenzofurans possessing a musky odour and fragrances and scented products containing them |
| WO2003010120A1 (en) * | 2001-07-20 | 2003-02-06 | Merck Patent Gmbh | Indane compounds with negative dielectric anisotropy |
-
0
- DE DENDAT279864D patent/DE279864C/de active Active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2421812A (en) * | 1939-07-14 | 1947-06-10 | Univ Minnesota | Method of producing chroman compounds |
| US2421811A (en) * | 1939-07-14 | 1947-06-10 | Univ Minnesota | Process for producing chroman compounds |
| US2548704A (en) * | 1949-08-17 | 1951-04-10 | Dow Chemical Co | Substituted 2,3-dihydro-2-methylbenzofurans |
| US2937188A (en) * | 1951-11-15 | 1960-05-17 | Gen Aniline & Film Corp | 2-methyl 2, 3-dihydrobenzofurancarboxylic acids and acid halides |
| FR2634203A1 (en) * | 1988-07-13 | 1990-01-19 | Inst Rech Controles Techn | 2,3-Dihydrobenzofurans possessing a musky odour and fragrances and scented products containing them |
| WO2003010120A1 (en) * | 2001-07-20 | 2003-02-06 | Merck Patent Gmbh | Indane compounds with negative dielectric anisotropy |
| US7122228B2 (en) | 2001-07-20 | 2006-10-17 | Merck Patent Gmbh | Compound having negative Δε |
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