CH143266A - Process for the preparation of a halogen naphthalene ketone. - Google Patents
Process for the preparation of a halogen naphthalene ketone.Info
- Publication number
- CH143266A CH143266A CH143266DA CH143266A CH 143266 A CH143266 A CH 143266A CH 143266D A CH143266D A CH 143266DA CH 143266 A CH143266 A CH 143266A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- dichloro
- naphthalene
- chlorobenzoyl
- condensation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052736 halogen Inorganic materials 0.000 title description 2
- -1 halogen naphthalene ketone Chemical class 0.000 title description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- COUXDYHQXSSNCX-UHFFFAOYSA-N (4-chlorophenyl)-(5,8-dichloronaphthalen-1-yl)methanone Chemical compound Clc1ccc(cc1)C(=O)c1cccc2c(Cl)ccc(Cl)c12 COUXDYHQXSSNCX-UHFFFAOYSA-N 0.000 claims description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 3
- AMCBMCWLCDERHY-UHFFFAOYSA-N 1,3-dichloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC(Cl)=C21 AMCBMCWLCDERHY-UHFFFAOYSA-N 0.000 description 1
- JDPKCYMVSKDOGS-UHFFFAOYSA-N 1,4-dichloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=C(Cl)C2=C1 JDPKCYMVSKDOGS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Halogennaphtalinketons. Gegenstand vorliegenden Patentes ist ein Verfahren zur Darstellung von 1,4-Dichlor- 8-(p-ehlorberizoyl)-rraphtalin, dadurch gekenn zeichnet, dass man 1,4-Dichlornaphtalirr mit p-Chlorbenzoylchlorid bei Anwesenheit von Aluminiumchlorid kondensiert.
1,4 - Dichlor - 8 -(p-chlorbenzoyl) - naphtalin kristallisiert aus Alkohol in farblosen Nadeln vom Schmelzpunkt<B>118'</B> C. Die Lösungs farbe in konzentrierter Schwefelsäure ist gelb. <I>Beispiel:</I> 100 Gewichtsteile 1,4-Dichlorrraphtalirr, 88 Gewichtsteile p-Chlorberrzoylchlorid, <B>135</B> Gewichtsteile Aluminiumchlorid werden in 500 Gewichtsteilen Schwefelkohlenstoff unter Rückfluss 20 Stunden auf dem Wasserbade gerührt. Das Reaktionsgemisch wird mit Eis wasser zersetzt, 2 Stunden mit Wasserdampf destilliert, dann zweimal mit verdünnter Salz säure und Wasser ausgekocht.
Nach dem Trocknen wird das harzartige Rohketon durch Vakuumdestillation von nicht umgesetztem Dichlornaphtalin gereinigt. Das so erhaltene zähe, gelbe<B>01</B> wird mit viel Alkohol verrie ben und so kristallisiert erhalten. Zur wei teren Reinigung kann noch aus Äthylalkohol umkristallisiert werden. Farblose Nadeln, Schmelzpunkt 1180. Ausbeute 75%.
Process for the preparation of a halogen naphthalene ketone. The subject of the present patent is a process for the preparation of 1,4-dichloro-8- (p-ehlorberizoyl) -rraphthalene, characterized in that 1,4-dichloronaphthalene is condensed with p-chlorobenzoyl chloride in the presence of aluminum chloride.
1,4 - dichloro - 8 - (p-chlorobenzoyl) - naphthalene crystallizes from alcohol in colorless needles with a melting point of <B> 118 '</B> C. The solution color in concentrated sulfuric acid is yellow. <I> Example: </I> 100 parts by weight 1,4-Dichlorrraphthalirr, 88 parts by weight p-Chlorberrzoylchlorid, <B> 135 </B> parts by weight aluminum chloride are stirred in 500 parts by weight carbon disulfide under reflux for 20 hours on the water bath. The reaction mixture is decomposed with ice water, distilled for 2 hours with steam, then boiled twice with dilute hydrochloric acid and water.
After drying, the resinous crude ketone is purified from unreacted dichloronaphthalene by vacuum distillation. The viscous, yellow <B> 01 </B> obtained in this way is triturated with a large amount of alcohol and thus obtained in crystallized form. For further purification can still be recrystallized from ethyl alcohol. Colorless needles, melting point 1180. Yield 75%.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE143266X | 1927-11-26 | ||
| CH141524T | 1930-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143266A true CH143266A (en) | 1930-10-31 |
Family
ID=25713768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143266D CH143266A (en) | 1927-11-26 | 1928-11-24 | Process for the preparation of a halogen naphthalene ketone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143266A (en) |
-
1928
- 1928-11-24 CH CH143266D patent/CH143266A/en unknown
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