CH205792A - Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. - Google Patents
Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide.Info
- Publication number
- CH205792A CH205792A CH205792DA CH205792A CH 205792 A CH205792 A CH 205792A CH 205792D A CH205792D A CH 205792DA CH 205792 A CH205792 A CH 205792A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxynaphthoic acid
- preparation
- acid arylide
- arylide
- highly substantive
- Prior art date
Links
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines hoehsubstantiven 2,3-Ogynaphthoesäurearylids. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Herstellung eines hochsubstantiven 2,3-Oxynaphthoesäureary- lids, welches dadurch gekennzeichnet ist, dass man 2,3-Oxynaphthoesäure mit 7-Chlor-2-ami- no-3-methoxy-diphenylenoxyd kondensiert.
Die erhaltene, bisher nicht bekannte Ver bindung stellt ein wertvolles Zwischenprodukt zur Herstellung von Farbstoffen dar.
<I>Beispiel:</I> 188 Gewichtsteile 2,3-Oxynaphthoesäure werden mit 247 Gewichtsteilen 7-Chlor-2- amino-3-methoxy-diphenylenoxyd und 2000 Gewichtsteilen Toluol unter Rühren auf 70 bis<B>80"</B> C erwärmt, und bei dieser Tempe ratur werden langsam 70 Gewichtsteile Phos. phortrichlorid zugetropft. Man hält dann das (*D'remisch noch etwa 8 Stunden im Sieden, nach dieser Zeit ist die Chlorwasserstoffent- wicklung praktisch beendet.
Nach Zusatz einer Lösung von 70 Gewichtsteilen Natrium- carbonat in 2000 Gewichtsteilen Wasser unter wirft man das Reaktionsgemisch einer Wasser- darnpfdestillation. Wenn alles Toluol abge- trieben ist, wird die Suspension heiss abge saugt und mit heissem Wasser gründlich ge waschen. Der Filterkuchen wird dann noch mit verdünnter Salzsäure ausgekocht, um geringe Mengen nicht umgesetzter Base zu entfernen.
Das erhaltene rohe 2-(2', 3'-Oxynaphtoyl- amirro) - 7- chlor- 3 - methoxy - diphenylenoxyd stellt nach dem Trocknen ein schwach ge färbtes Pulver dar, das aus Chlorbenzol oder Eisessig in feinen Nadeln vom F. 268-270 C kristallisiert.
Process for the preparation of a highly substantial 2,3-ogynaphthoic acid arylide. The subject of the present additional patent is a process for the production of a highly substantive 2,3-oxynaphthoic acid arylide, which is characterized in that 2,3-oxynaphthoic acid is condensed with 7-chloro-2-amino-3-methoxydiphenylene oxide.
The compound obtained, previously unknown, is a valuable intermediate for the production of dyes.
<I> Example: </I> 188 parts by weight of 2,3-oxynaphthoic acid are mixed with 247 parts by weight of 7-chloro-2-amino-3-methoxydiphenylene oxide and 2000 parts by weight of toluene to 70 to 80 "</ B with stirring > C, and at this temperature 70 parts by weight of phosphorus trichloride are slowly added dropwise. The mixture is then kept boiling for about 8 hours, after which time the evolution of hydrogen chloride is practically complete.
After adding a solution of 70 parts by weight of sodium carbonate in 2000 parts by weight of water, the reaction mixture is subjected to a water distillation. When all the toluene has been driven off, the suspension is sucked off while hot and washed thoroughly with hot water. The filter cake is then boiled with dilute hydrochloric acid in order to remove small amounts of unreacted base.
The crude 2- (2 ', 3'-Oxynaphtoyl- amirro) - 7- chloro- 3 - methoxy - diphenylene oxide is after drying a weakly colored powder, which is made of chlorobenzene or glacial acetic acid in fine needles of F. 268- 270 C crystallizes.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE205792X | 1936-02-19 | ||
| DE205790X | 1936-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205792A true CH205792A (en) | 1939-06-30 |
Family
ID=32963187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205792D CH205792A (en) | 1936-02-19 | 1937-02-15 | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205792A (en) |
-
1937
- 1937-02-15 CH CH205792D patent/CH205792A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH205792A (en) | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. | |
| CH205791A (en) | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. | |
| CH205790A (en) | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. | |
| CH205794A (en) | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. | |
| CH205793A (en) | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. | |
| DE726431C (en) | Process for the preparation of arylides from ª ‰ -ketone carboxylic acids | |
| CH218517A (en) | Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isopropyl-ketone. | |
| DE523692C (en) | Process for the preparation of aminosulfonic acid arylamides of 2íñ3-oxynaphthoic acid | |
| DE650432C (en) | Process for the preparation of diarylamines | |
| CH186446A (en) | Process for the preparation of an arylamide. | |
| CH175236A (en) | Process for the preparation of 1,3,5-di- (p-methoxyphenylamino) -oxybenzene. | |
| CH201953A (en) | Process for the preparation of terephthaloyl 1- (4'-nitranilide) -4-chloride. | |
| CH148353A (en) | Process for the preparation of an m-oxy-phenylarylamine carboxylic acid. | |
| CH204236A (en) | Process for the preparation of a 2,3-oxynaphthoic acid arylide. | |
| CH143279A (en) | Process for the preparation of a 6-arylamino-2-naphthol-3-carboxylic acid. | |
| CH181804A (en) | Process for the preparation of an arylamide. | |
| CH186445A (en) | Process for the preparation of an arylamide. | |
| CH154992A (en) | Process for the preparation of a diacylated diamine. | |
| CH222973A (en) | Process for the preparation of a mixed urea with solubilizing groups. | |
| CH162037A (en) | Process for the preparation of a non-coloring thio derivative of phenol. | |
| CH209497A (en) | Process for the preparation of a 2,3-oxynaphthoic acid arylide. | |
| CH93489A (en) | Process for the preparation of a heterocyclic compound of the naphthalene series. | |
| CH187935A (en) | Process for the preparation of an acridinium compound. | |
| CH163180A (en) | Process for the preparation of triallylacetonitrile. | |
| CH110427A (en) | Process for the preparation of an alkamine ester of an aromatic aminocarboxylic acid. |