CH243100A - Process for the preparation of α-naphthylacetic acid. - Google Patents
Process for the preparation of α-naphthylacetic acid.Info
- Publication number
- CH243100A CH243100A CH243100DA CH243100A CH 243100 A CH243100 A CH 243100A CH 243100D A CH243100D A CH 243100DA CH 243100 A CH243100 A CH 243100A
- Authority
- CH
- Switzerland
- Prior art keywords
- naphthylacetic acid
- naphthalene
- dichloromethyl ether
- preparation
- acid
- Prior art date
Links
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims 5
- 238000002360 preparation method Methods 0.000 title description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 claims description 6
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- OQRMWUNUKVUHQO-UHFFFAOYSA-N 2-naphthalen-1-ylacetonitrile Chemical compound C1=CC=C2C(CC#N)=CC=CC2=C1 OQRMWUNUKVUHQO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- -1 alkali metal cyanide Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Torfahren zur Herstellung von a-Naphthylessigsäure. Es wurde gefunden, dass man a-Naph- thylessigsäure auf sehr einfache Weise und viel billiger als bisher herstellen kann, wenn man gemäss der vorliegenden Erfindung Naphthalin in schwefelsaurer Lösung Di- chlormethyläther (Cl .<B>CH,</B> - 0 - CH, Cl) zusetzt,
das entstandene a-Chlormethylnaph- thalin mit Alkalicyanid in das Nitril über führt und letzteres. zu a-Naphthylessigsäure verseift.
Vorzugsweise verwendet man eine Lösung von Naphthalin in zirka 40 % iger Schwefel säure und führt die Umsetzung mit dem Di- ehlormethyläther unter Rühren bei einer Temperatur von 60-65 C durch.
Beispiel: Zu einer Lösung von 128 g Naphthalin in 14 g konzentrierter Schwefelsäure und 35 g Wasser werden tropfenweise und unter Rüh ren 114 g Dichlormethyläther zugegeben und das Reaktionsgemisch dann 24 Stunden lang weiter gerührt, wobei es während dieser gan zen Zeit auf einer Temperatur von 60-65 C gehalten wird. Dann wird das entstandene a-Chlormethylnaphthalin abgetrennt, mit Wasser gewaschen und in bekannter Weise mit Natriumcyanid umgesetzt. Das entstandene Naphthylacetonitril wird alkalisch zu a-Naph- thylessigsäure verseift.
Soll letztere in Form ihres Natriumsalzes zur Verwendung gelangen, so wird sie zweck mässigerweise in so viel Natronlauge gelöst, dass die entstehende Lösung gerade den pH-Wert 7 aufweist. Hierzu sind bei Verwen dung von 1 n Na<B>01 197,5</B> % der äquivalenten Menge und bei Verwendung von 0,1n Na OH 99 % der äquivalenten Menge erforderlich. Man verwendet also jeweils auf 186 g a-Naph- thylessigsäure entweder 975 cm' 1 n Na OH oder 9900 cm3 0,1n Na OH. Die Lösung wird zur Trockne verdampft und der Rückstand gepulvert .sowie nochmals scharf getrocknet.
Das erhaltene Präparat ist unter Ausschluss von Feuchtigkeit aufzubewahren. Aus der Lösung des Natriumsalzes kann die freie a-Naphthylessigsäure durch Zugabe von kon zentrierter Salzsäure wieder abgeschieden werden.
Tor driving for the production of a-naphthylacetic acid. It has been found that a-naphthylacetic acid can be produced in a very simple way and much cheaper than before if, according to the present invention, naphthalene in a sulfuric acid solution is dichloromethyl ether (Cl. CH, - 0 - CH, Cl) adds,
the resulting α-chloromethylnaphthalene with alkali metal cyanide converts into nitrile and the latter. saponified to a-naphthylacetic acid.
A solution of naphthalene in approximately 40% strength sulfuric acid is preferably used and the reaction with the dichloromethyl ether is carried out at a temperature of 60-65 ° C. with stirring.
Example: 114 g of dichloromethyl ether are added dropwise and with stirring to a solution of 128 g of naphthalene in 14 g of concentrated sulfuric acid and 35 g of water and the reaction mixture is then stirred for a further 24 hours, during which time it is kept at a temperature of 60 -65 C. The α-chloromethylnaphthalene formed is then separated off, washed with water and reacted in a known manner with sodium cyanide. The resulting naphthylacetonitrile is saponified under alkaline conditions to give α-naphthylacetic acid.
If the latter is to be used in the form of its sodium salt, it is expediently dissolved in enough sodium hydroxide solution that the resulting solution just has a pH of 7. For this purpose, when using 1N Na 01 197.5% of the equivalent amount and when using 0.1N Na OH 99% of the equivalent amount are required. Either 975 cm -1 N Na OH or 9900 cm 3 0.1 N Na OH are used for each 186 g of a-naphthylacetic acid. The solution is evaporated to dryness and the residue is powdered and dried again sharply.
The preparation obtained must be stored in the absence of moisture. The free α-naphthylacetic acid can be separated out again from the solution of the sodium salt by adding concentrated hydrochloric acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH243100T | 1944-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH243100A true CH243100A (en) | 1946-06-30 |
Family
ID=4463341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH243100D CH243100A (en) | 1944-12-28 | 1944-12-28 | Process for the preparation of α-naphthylacetic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH243100A (en) |
-
1944
- 1944-12-28 CH CH243100D patent/CH243100A/en unknown
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