CH98559A - Process for the preparation of an aryloxynaphthyl ketone. - Google Patents
Process for the preparation of an aryloxynaphthyl ketone.Info
- Publication number
- CH98559A CH98559A CH98559DA CH98559A CH 98559 A CH98559 A CH 98559A CH 98559D A CH98559D A CH 98559DA CH 98559 A CH98559 A CH 98559A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzotrichloride
- ketone
- carboxylic acid
- act
- oxynaphthyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000002576 ketones Chemical class 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003518 caustics Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- -1 aryloxy naphthyl ketone Chemical compound 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000725 suspension 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Aryloxynaphthylketons. Es wurde gefunden, dass man ein Aryl- oxynaphthylketon herstellen kann, wenn man auf 1-Oxynaphthalin-2-carbonsäure, mit oder ohne Zusatz von Verdünnungs- bezw. Kon densationsmitteln, aber unter Ausschluss von Alkalien, Benzotrichlorid einwirken lässt.
Die so gewonnene 1-Phenylketon-4-oxynaphthyl- 3-carbonsäure bildet weisse Nadeln, die bei 205 unter Zersetzung schmelzen und sich in Ätzalkalien und in konz. Schwefelsäure mit gelber Farbe lösen.
<I>Beispiel 1:</I> 19,5 Teile Benzotrichlorid und 18,8 Teile 1-Oxynaphthalin-2-carbonsäure werden bei Zimmertemperatur in 100 Teile konz. Schwefel säure eingetragen und so lange zusammen gerührt, bis sich keine Salzsäure mehr ent wickelt.
Hierauf giesst man in Wasser, fil triert die ausgeschiedene 1-Pherrylketon-4- oxynaphthyl-3-carbonsäure ab und reinigt sie durch Umkristallisieren ihres Natriumsalzes. <I>Beispiel 2</I> 188 Teile 1-Oxynaphtalin-2-carbonsäure werden in 230 Teile Benzotrichlorid einge- tragen; die entstandene Lösung wird so lange auf 100-1200 erwärmt, bis keine Salzsäure mehr entweicht.
Hierauf wird das über schüssige Benzotrichlorid im Vakuum ab destilliert, der Rückstand, zwecks Verseifung allfällig gebildeter Hydroxyl-gondensations- produkte mit verdünnter Natronlauge einige Zeit aufgekocht. Die entstandene Lösung wird filtriert und mit Säure versetzt, wobei die 1-Phenylketon-4-oxynaphtalin-3-carbon- säure als weisse Masse ausfällt.
<I>Beispiel 3:</I> 18,8 Teile 1-Oxynaphthalin-2-carbonsäure, in 30 Teilen Nitrobenzol suspendiert, werden mit 10 Teilen Monohydrat, hierauf nach und nach mit 19,5 Teilen Benzotrichlorid versetzt. Am folgenden Tage wird mit Wasser ge schüttelt und die Nitrobenzolschicht, welche das Keton suspendiert enthält, abgetrennt und filtriert. Der Rückstand wird in verdünnter Natronlauge gelöst, abfiltriert, die Lösung ausgesäuert und die ausfallende 1-Phenyl- keton-4-oxynaphthyl-3-carbonsäure aus Essig säure umgelöst.
Process for the preparation of an aryloxynaphthyl ketone. It has been found that an aryl oxynaphthyl ketone can be produced if one responds to 1-oxynaphthalene-2-carboxylic acid, with or without the addition of diluent. Condensation agents, but with the exclusion of alkalis, benzotrichloride can act
The 1-phenylketone-4-oxynaphthyl-3-carboxylic acid obtained in this way forms white needles, which melt at 205 with decomposition and dissolve in caustic alkalis and in conc. Dissolve sulfuric acid with yellow color.
<I> Example 1: </I> 19.5 parts of benzotrichloride and 18.8 parts of 1-oxynaphthalene-2-carboxylic acid are concentrated in 100 parts at room temperature. Sulfuric acid entered and stirred together until no more hydrochloric acid develops.
It is then poured into water, the precipitated 1-Pherrylketon-4-oxynaphthyl-3-carboxylic acid is filtered off and it is purified by recrystallizing its sodium salt. <I> Example 2 </I> 188 parts of 1-oxynaphthalene-2-carboxylic acid are introduced into 230 parts of benzotrichloride; the resulting solution is heated to 100-1200 until no more hydrochloric acid escapes.
The excess benzotrichloride is then distilled off in vacuo, and the residue, for the purpose of saponifying any hydroxyl condensation products that may have formed, is boiled with dilute sodium hydroxide for some time. The resulting solution is filtered and acid is added, the 1-phenylketone-4-oxynaphthalene-3-carboxylic acid precipitating as a white mass.
<I> Example 3: </I> 18.8 parts of 1-oxynaphthalene-2-carboxylic acid, suspended in 30 parts of nitrobenzene, are mixed with 10 parts of monohydrate and then gradually with 19.5 parts of benzotrichloride. The following day, it is shaken with water and the nitrobenzene layer, which contains the ketone in suspension, is separated off and filtered. The residue is dissolved in dilute sodium hydroxide solution, filtered off, the solution is acidified and the 1-phenyl-ketone-4-oxynaphthyl-3-carboxylic acid which precipitates is redissolved from acetic acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH98559T | 1921-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH98559A true CH98559A (en) | 1923-04-02 |
Family
ID=4356405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH98559D CH98559A (en) | 1921-09-24 | 1921-09-24 | Process for the preparation of an aryloxynaphthyl ketone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH98559A (en) |
-
1921
- 1921-09-24 CH CH98559D patent/CH98559A/en unknown
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