DE111656C - - Google Patents
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- Publication number
- DE111656C DE111656C DENDAT111656D DE111656DA DE111656C DE 111656 C DE111656 C DE 111656C DE NDAT111656 D DENDAT111656 D DE NDAT111656D DE 111656D A DE111656D A DE 111656DA DE 111656 C DE111656 C DE 111656C
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- salol
- acid
- salicylic acid
- phenol
- 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.)
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 20
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 6
- 229960004889 salicylic acid Drugs 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 3
- 150000004780 naphthols Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N Phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 9
- 229960000969 phenyl salicylate Drugs 0.000 description 9
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 5
- -1 disalicylic acid resorcinol ester Chemical class 0.000 description 5
- 229960000583 Acetic Acid Drugs 0.000 description 4
- 239000005770 Eugenol Substances 0.000 description 4
- 229960002217 Eugenol Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229960001755 resorcinol Drugs 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RECUKUPTGUEGMW-UHFFFAOYSA-N Carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N M-Cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- ZEOIBEYTZWKXFD-UHFFFAOYSA-N Oc1ccc(O)c(Cc2ccccc2O)c1 Chemical compound Oc1ccc(O)c(Cc2ccccc2O)c1 ZEOIBEYTZWKXFD-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N p-acetaminophenol Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- DLGBEGBHXSAQOC-UHFFFAOYSA-N 2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC=C(O)C(C(O)=O)=C1 DLGBEGBHXSAQOC-UHFFFAOYSA-N 0.000 description 1
- RPWICXJPQJJQPC-UHFFFAOYSA-N 2-hydroxybenzoic acid;2-methoxy-4-prop-2-enylphenol Chemical class OC(=O)C1=CC=CC=C1O.COC1=CC(CC=C)=CC=C1O RPWICXJPQJJQPC-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- RYCFMZJEPVLDKR-UHFFFAOYSA-N C=1(C(O)=CC=C(C)C1)C(=O)OC1=CC(OC(=O)C=2C(O)=CC=C(C)C2)=CC=C1 Chemical compound C=1(C(O)=CC=C(C)C1)C(=O)OC1=CC(OC(=O)C=2C(O)=CC=C(C)C2)=CC=C1 RYCFMZJEPVLDKR-UHFFFAOYSA-N 0.000 description 1
- PETRWTHZSKVLRE-UHFFFAOYSA-N Creosol Chemical compound COC1=CC(C)=CC=C1O PETRWTHZSKVLRE-UHFFFAOYSA-N 0.000 description 1
- 229960002126 Creosote Drugs 0.000 description 1
- 241000735588 Gaultheria Species 0.000 description 1
- 229960001867 Guaiacol Drugs 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- 240000007588 Larrea tridentata Species 0.000 description 1
- 229940079877 Pyrogallol Drugs 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- MGSRCZKZVOBKFT-UHFFFAOYSA-N Thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- GGISZLOBBISXOZ-UHFFFAOYSA-N acetic acid;chloroform Chemical compound CC(O)=O.ClC(Cl)Cl GGISZLOBBISXOZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000007746 carvacrol Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229930007823 thymol Natural products 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Höhere Salole können erhalten werden, wenn man Salicylsäurephenylester (»Salol«) mit höheren Phenolen erhitzt. Das niedrigere Phenol wird aus dem Molecule verdrängt. Die Reaction verläuft beispielsweise nach der Gleichung: Higher salols can be obtained by using phenyl salicylate ("Salol") with higher phenols heated. The lower phenol is displaced from the molecule. the For example, reaction proceeds according to the equation:
rr/OH ■ r rr / OH ■ r
■>Mi\CO2- C6H5 + Cl»· ■> Mi \ C O 2 - C 6 H 5 + Cl »·
QH.OH + QH,<QH.OH + QH, <
OHOH
%0H = % 0H =
CTJCTJ
Dieses Verhalten des Salicylsäurephenylesters ist neu. Die Ausbeuten sind meist sehr gut, und die Reinigung der Verbindungen bietet keine Schwierigkeiten.This behavior of the salicylic acid phenyl ester is new. The yields are usually very good, and the cleaning of the connections presents no difficulties.
Von technischem Werthe ist die Methode besonders dann, wenn man es mit empfindlichen Phenolen zu thun hat, die die Anwendung der sonst üblichen Condensationsmittel (CO Cl2, PO Cl3 u. s. w.) nicht ertragen, ohne Zersetzung und Verharzung zu erleiden. So ist es auf dem neuen Wege möglich, Salicylsäureeugenolester, der in der Medicin Anwendung finden soll, mühelos zu gewinnen, während seine directe Darstellung aus Salicylsäure und Eugenol bisher nicht gelungen ist.The method is of technical value especially when one has to deal with sensitive phenols which can not bear the use of the usual condensation agents (CO Cl 2 , PO Cl 3, etc.) without suffering from decomposition and resinification. Thus it is possible in the new way to obtain salicylic acid eugenol esters, which are to be used in medicine, effortlessly, while its direct preparation from salicylic acid and eugenol has so far not been successful.
Ein weiterer Vorzug des Verfahrens liegt darin, dafs es gestattet, die Monosalicylsäureester zweiwerthiger Phenole (z. B. des Resörcins) glatter zu gewinnen, als es bisher möglich war. Bei der Condensation molecularer Mengen Salicylsäure und Resorcin mittels Phosphoroxychlorid enthält das Reactionsproduct nicht unbeträchtliche Mengen des Disalicylsäureresorcinesters. Another advantage of the process is that it allows the monosalicylic acid esters To obtain dihydric phenols (e.g. Resörcin) more smoothly than was previously possible was. In the condensation of molecular quantities of salicylic acid and resorcinol by means of phosphorus oxychloride, the reaction product contains not inconsiderable amounts of the disalicylic acid resorcinol ester.
Schliefslich ist bei der neuen Salolgewinnung die Bildung phosphorhaltiger Nebenproducte, die bei dem alten Verfahren in mehr oder minder , grofser Menge störend auftreten und die Ausbeute vermindern, unmöglich, so dafs auch in dieser Beziehung die neue Methode der bisherigen überlegen ist.Finally, the formation of phosphorus-containing by-products in the new salol production which, in the old method, are more or less disturbing and reducing the yield is impossible, so in this respect too the new method is superior to the previous one.
Die Reaction ist keine allgemeine. Sie versagt z. B., wenn man das Phenol durch Salicylsäure, Gaultheriaöl u. s. w. austreiben will. Folgende Phenole verdrängen beispielsweise den Phenolrest aus dem Salol: m-Kresol, die Nitrophenole, o- und p-Chlorphenol, p-Amidophenol, p-Acetamidophenol, Thymol und Carvacrol, α- und ß-Naphtol, Guajakol, Brenzcatechinmonoäthyläther, Kreosol, Kreosot, Eugenol, Resorcin und Pyrogallol, Salicylamid u. a. Wie Salol verhalten sich auch die homologen Kresotinsäurephenylester, ferner die Kresolester u. s. w. den complicirter zusammengesetzten Phenolen und den Naphtolen gegenüber. The reaction is not a general one. You fail z. B. If you replace the phenol with salicylic acid, Gaultheria oil and so on. For example, the following phenols displace the phenol residue from Salol: m-cresol, the nitrophenols, o- and p-chlorophenol, p-amidophenol, p-acetamidophenol, thymol and carvacrol, α- and ß-naphtol, guaiacol, catechol monoethyl ether, Creosol, creosote, eugenol, resorcinol and pyrogallol, salicylamide and others. The homologues behave like Salol Phenyl cresotinate, also the cresol esters, and so on, the more complex compounds Phenols and the naphthols.
Beispiel 1. Berechnete Mengen Salol und Eugenol werden etwa 1 Stunde auf 190 bis 200° erhitzt. Man verjagt das abgespaltene Phenol und überschüssiges Eugenol durch Wasserdampf und rührt das auf üblichem Wege isolirte ölige Reactionsproduct mit wenig Alkohol an. Das Salicyleugenol scheidet sich bald in Krystallen ab. Es wird aus Alkohol umkrystallisirt. . .Example 1. Calculated quantities Salol and Eugenol will be at 190 to about 1 hour Heated to 200 °. The split off phenol and excess eugenol are chased through Steam and stir the oily reaction product isolated in the usual way with little Alcohol. The salicyleugenol soon separates out in crystals. It becomes alcohol recrystallized. . .
Beispiel 2. 5 Theile Salol werden mit 3,6 Theilen Acetamidophenol 1 bis 2 Stunden auf 200 bis 2io° erhitzt. Das mit Wasser behandelte Reactionsproduct erstarrt schnell, wirdExample 2. 5 parts of Salol are mixed with 3.6 parts of acetamidophenol for 1 to 2 hours heated to 200 to 2io °. The reaction product treated with water solidifies quickly and becomes
getrocknet und durch Verreiben mit etwas Benzol in ein weifses krystallinisches Pulver übergeführt, das aus Alkohol oder Benzol umkrystallisirt wird. Schmp. 185°. Identisch mit Salicylacetamidophenoldried and by rubbing with a little benzene into a white crystalline powder which is recrystallized from alcohol or benzene. M.p. 185 °. Identical with Salicylacetamidophenol
OHs CH3 — CO — NH-( y~ 0—CO-1 OHs CH 3 - CO - NH- (y ~ 0-CO- 1
Beispiel 3. Ein Gemisch von 5 Theilen Salol und 4 Theilen m-Kresol wird i3/4 Stunden lang in gelindem Sieden erhalten, dann mit Wasserdampf behandelt. Der nicht flüchtige Bestandtheil erstarrt nach einigen Tagen und giebt, mit etwas Alkohol übergössen, das bei etwa jo° schmelzende Salicyl-m-Kresol in quantitativer Ausbeute.Example 3. A mixture of 5 parts salol and 4 parts of m-cresol is i obtained in gently boiling 3/4 hours, then treated with water vapor. The non-volatile constituent solidifies after a few days and, poured over with a little alcohol, gives the salicyl-m-cresol , which melts at about 5 °, in quantitative yield.
Beispiel 4. 15 Theile Salol und 10 Theile Hydrochinon werden 2 Stunden lang, erst auf 220°, später bis auf 2600 erhitzt. Das frei werdende Phenol destillirt schnell ab. Die Schmelze wird mit Wasser behandelt, um unverändertes Hydrochinon zu entfernen, und dann mit Alkohol ausgekocht. Ungelöst bleibt etwas Disalicylhydrochinon, während das Hauptproduct, Monosalicylhydrochinon, im Filtrat enthalten ist und auf üblichem Wege isolirt wird.Example 4. 15 parts salol and 10 parts of hydroquinone are 2 hours, first at 220 ° heated later to 260 0th The released phenol distills off quickly. The melt is treated with water to remove unchanged hydroquinone and then boiled with alcohol. Some disalicylhydroquinone remains undissolved, while the main product, monosalicylhydroquinone, is contained in the filtrate and isolated in the usual way.
Die angegebenen Mengen-, Zeit- und Temperaturverhältnisse können innerhalb weiter Grenzen schwanken. Die mit Naphtolen und anderen höheren Phenolen erhaltenen Körper krystallisiren meist schon, sobald das freie Phenol durch Destillation, durch Waschen mit Wasser oder durch Wasserdampf entfernt worden ist. Sämmtliche Salole werden durch heifse Alkalilauge in Salicylsäure und das betreffende Phenol zerlegt.The specified quantity, time and temperature ratios can vary within wide limits. The bodies obtained with naphthols and other higher phenols usually crystallize as soon as the free phenol is distilled or washed with Removed by water or steam. All saloles are through hot alkali is broken down into salicylic acid and the phenol in question.
Nach dem angegebenen Verfahren wurden u. A. folgende bisher nicht bekannte Salole erhalten:The following hitherto unknown salols, among others, were produced using the specified process obtain:
Salicyleugenol,Salicyleugenol,
QH,QH,
OCH3 OCH 3
OO CO— QH,CO— QH,
feine Prismen aus Alkohol, in dem sie ziemlich schwer löslich sind. Schmp. 730. Die Verbindung löst sich in concentrirter Schwefelsäure mit schön eosinrother Farbe und giebt mit Eisenchlorid eine weinrothe Färbung.fine prisms made of alcohol, in which they are rather difficult to dissolve. M.p. 73 0 . The compound dissolves in concentrated sulfuric acid with a beautiful eosine-red color, and gives a wine-red color with ferric chloride.
Disalicylhydrochinon,Disalicylhydroquinone,
^-O—CO—QH^ -O-CO-QH
— O— CO-C6H1 - O- CO-C 6 H 1
, OH , OH
Schmp. 150 bis 1510, krystallisirt aus heifsem Eisessig in charakteristisch gezackten Blättern, die in kochendem Alkohol sehr wenig, in Aceton und heifsem Eisessig reichlich löslich sind.Melting point 150 to 151 0 , crystallized from hot glacial acetic acid in characteristically jagged leaves, which are very little soluble in boiling alcohol and abundantly soluble in acetone and hot glacial acetic acid.
Monosalicylhydrochinon,
OH Monosalicylhydroquinone,
OH
weifse Blättchen, in den meisten Solventien leicht, in Benzin sehr schwerlöslich. Schmp. 96 bis-0,80. Die alkoholische Lösung wird durch Eisenchlorid rothbraun gefärbt.white flakes, easily soluble in most solvents, very sparingly soluble in gasoline. M.p. 96 to -0.8 0 . The alcoholic solution is colored red-brown by iron chloride.
Salicylcarvacrol,
C3H7 Salicylcarvacrol,
C 3 H 7
OHS OH S
QH,QH,
sehr dickflüssiges, schwach gelblich gefärbtes OeI, das nicht zum Krystallisireh gebracht werden konnte.very viscous, pale yellowish colored oil, which cannot be crystallized could.
Salicylsalicylamid,Salicylsalicylamide,
CO-NH2 CO-NH 2
\0\ 0
C0 OHC0 OH
vielleicht identisch mit Disalicylamid, lange hellgelbe Nadeln (aus Alkohol) vom Schmp. 2030, die sich, mit Natronlauge Übergossen, tief gelb färben und beim Erhitzen mit Alkali in Salicylsäure und Ammoniak zerfallen.Perhaps identical to disalicylamide, long pale yellow needles (made from alcohol) of m.p. 203 0 , which, when doused with caustic soda, turn a deep yellow and disintegrate into salicylic acid and ammonia when heated with alkali.
Di-p-kresotinsäureresorcinester,Resorcinol di-p-cresotinate,
^0-CO-QH3-CH3 ^ 0-CO-QH 3 -CH 3
I-'O— CO — QH3- I-'O— CO - QH 3 -
feine, kugelförmig gruppirte Nadeln, Schmp. 106 bis 1070; Färbung mit Eisenchlorid grünlich braun, wenig charakteristisch.fine, spherically grouped needles, m.p. 106 to 107 0 ; Colored greenish brown with ferric chloride, not very characteristic.
Di-p-kresotinsäurehydrochinonester,Di-p-cresotinic acid hydroquinone ester,
— CH- CH
0-CO-C6H3-CH3 O-CO-C 6 H 3 -CH 3
krystallisirt aus Eisessig in langen, büschelförmig gruppirten Nadeln vom Schmp. 197 bis 1980, die in Aether und Aceton schwer, in Alkohol spurenweise löslich sind.Crystallizes from glacial acetic acid in long, cluster-shaped needles of m.p. 197 to 198 0 , which are sparingly soluble in ether and acetone, and in traces in alcohol.
p-Kresotinsäure-ß-napht öl ester,p-cresotinic acid-ß-naphtho oil ester,
OHx OH x
O—CO— C6H3- CH3 '
weifses, undeutlich krystallinisches Pulver o'der O — CO— C 6 H 3 - CH 3 '
white, indistinct crystalline powder or
schimmernde Blättchen aus Alkohol, Schmp. 103 bis 104°; Färbung mit Eisenchlorid violett, schnell in schmutzig-grün übergehend. Die Verbindung ist in Aether, Aceton, Chloroform und Eisessig sehr leicht löslich.shimmering leaves made of alcohol, m.p. 103 to 104 °; Staining with ferric chloride violet, quickly changing to dirty green. The compound is in ether, acetone, chloroform and glacial acetic acid very easily soluble.
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