CH132802A - Process for the preparation of a halogenated and alkylated arylthioglycolic acid. - Google Patents
Process for the preparation of a halogenated and alkylated arylthioglycolic acid.Info
- Publication number
- CH132802A CH132802A CH132802DA CH132802A CH 132802 A CH132802 A CH 132802A CH 132802D A CH132802D A CH 132802DA CH 132802 A CH132802 A CH 132802A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- chlorobenzene
- dimethyl
- preparation
- arylthioglycolic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 5
- KUZJZXMZFGUCLG-UHFFFAOYSA-N 2-(4-chloro-2,5-dimethylphenyl)-2-sulfanylacetic acid Chemical compound CC1=CC(C(S)C(O)=O)=C(C)C=C1Cl KUZJZXMZFGUCLG-UHFFFAOYSA-N 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- KZNRNQGTVRTDPN-UHFFFAOYSA-N 2-chloro-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(Cl)=C1 KZNRNQGTVRTDPN-UHFFFAOYSA-N 0.000 claims description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000004571 lime Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer halogenierten und alkylierten Arylthioglykolsäure. Vorliegendes Patent bezieht sich auf ein Verfahren zur Darstellung der 1.
4-Dimethyl- 2-chlorbenzol-5-thioglykolsäure der Formel
EMI0001.0007
dadurch gekennzeichnet, dass man auf 1.4- Dimethyl-2-ohlorbenzol Chlorsulfonsäure bei Temperaturen unter 100 einwirken lässt, das so erhaltene 1.4-Dimethyl-2-chlorbenzol-5- sulfochlorid zum Merkaptan reduziert und letzteres mit Monochloressigsäure konden siert.
Die so erhaltene 1.4-Dimethyl-2-chlor- benzol-5-thioglykolsäure schmilzt in reinem Zustand bei 96 . Beispiel: <I>a) Darstellung von 1.</I> 4-Dinzetlzyl-2-chlo2-berzzol- 5-sztl fochlor-id.
7 Teile 1.4-Dimethyl-2-chlorbenzol (Siede punkt 192 ) lässt man unter Rühren bei etwa 30-351 in etwa 30 Teile Chlorsulfon- säure langsam einfliessen. Man hält die Masse einige Stunden unter Rühren bei etwa<B>60'.</B> Nach dem Erkalten giesst man auf Eis, wobei sich das gebildete 1.4-Dimethyl-2-chlorbenzol- 5-sulfochlorid in kristalliner Form abscheidet. Die bisher unbekannte neue Verbindung kann unmittelbar weiter verarbeitet werden. Aus . Aceton umkristallisiert, schmilzt sie bei 50 .
<I>b)</I> Darstellung <I>von</I> 1.4-Dimethyl-2-chlorbenzol- 5-merkaptan. 24 Teile des oben beschriebenen Sulfo- chlorids werden in ein Gemisch von etwa 55 Teilen Schwefelsäure 66<B>0</B> B6 und 120 Teilen Wasser eingetragen und allmählich etwa 30 Teile Zinkstaub unter Rühren zu gesetzt, wobei man die Temperatur vorteilhaft bei<B>800</B> hält. Die Reduktion erfolgt hierbei glatt. Nach dem Erkalten scheidet sich das erhaltene Merkaptan als Kristallmasse ab, die durch Filtrieren von der Flüssigkeit abgetrennt wird.
Es ist zur Weiterverarbeitung in das Thioglykolsäurederivat ohne weiteres verwendbar. Will man es in chemisch reiner Form erhalten, so unterwirft man es vorteil haft einer Destillation mit Wasserdampf.
<I>c)</I> Darstellung <I>der 1.</I> 4-Dinaethyl-2-chdorbenzol- 5-thioylykolsäure. <B>17,3</B> Teile des so erhaltenen Merkaptans werden in verdünnter Natronlauge gelöst, hierzu gibt man bei gewöhnlicher Temperatur die äquivalente Menge Monochloressigsäure (10,7 Teile) in Form des Natronsalzes und digeriert die Mischung, bis die Merkaptan- reaktion verschwunden ist.
Die erhaltene 1.4- Dimethyl-2-chlorbenzol-5-thiogly kolsäurekann entweder in Form des schwerlöslichen Natron- oder Kalksalzes durch Aussalzen oder Aus kalken gewonnen werden, oder durch An- säuern der abgekühlten Lösung als freie Säure abgeschieden werden.
Process for the preparation of a halogenated and alkylated arylthioglycolic acid. The present patent relates to a method for displaying FIG.
4-Dimethyl-2-chlorobenzene-5-thioglycolic acid of the formula
EMI0001.0007
characterized in that chlorosulfonic acid is allowed to act on 1,4-dimethyl-2-chlorobenzene at temperatures below 100, the 1,4-dimethyl-2-chlorobenzene-5-sulfochloride thus obtained is reduced to mercaptan and the latter is condensed with monochloroacetic acid.
The 1,4-dimethyl-2-chlorobenzene-5-thioglycolic acid obtained in this way melts in the pure state at 96. Example: <I> a) Representation of 1. </I> 4-Dinzetlzyl-2-chlo2-berzzol- 5-sztl fochlor-id.
7 parts of 1,4-dimethyl-2-chlorobenzene (boiling point 192) are allowed to flow slowly into about 30 parts of chlorosulfonic acid at about 30-351 while stirring. The mass is kept for a few hours with stirring at about 60 '. After cooling, it is poured onto ice, the 1,4-dimethyl-2-chlorobenzene-5-sulfochloride formed separating out in crystalline form. The previously unknown new connection can be processed further immediately. Out . Recrystallized acetone, it melts at 50.
<I> b) </I> Representation <I> of </I> 1,4-dimethyl-2-chlorobenzene-5-mercaptan. 24 parts of the sulfochloride described above are introduced into a mixture of about 55 parts of sulfuric acid 66 B6 and 120 parts of water and about 30 parts of zinc dust are gradually added with stirring, the temperature advantageously being < B> 800 </B> lasts. The reduction takes place smoothly. After cooling, the mercaptan obtained separates out as a crystal mass, which is separated from the liquid by filtration.
It can easily be used for further processing into the thioglycolic acid derivative. If you want to get it in chemically pure form, it is advantageously subjected to distillation with steam.
<I> c) </I> Representation of <I> the 1st </I> 4-dinaethyl-2-chlorobenzene-5-thioylycolic acid. <B> 17.3 </B> parts of the mercaptan obtained in this way are dissolved in dilute sodium hydroxide solution, the equivalent amount of monochloroacetic acid (10.7 parts) in the form of the sodium salt is added to this at normal temperature and the mixture is digested until the mercaptan reaction has disappeared.
The 1,4-dimethyl-2-chlorobenzene-5-thioglycolic acid obtained can either be obtained in the form of the sparingly soluble sodium or lime salt by salting out or lime out, or separated out as the free acid by acidifying the cooled solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE132802X | 1926-11-24 | ||
| CH131360T | 1927-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH132802A true CH132802A (en) | 1929-04-30 |
Family
ID=25711614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH132802D CH132802A (en) | 1926-11-24 | 1927-11-10 | Process for the preparation of a halogenated and alkylated arylthioglycolic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH132802A (en) |
-
1927
- 1927-11-10 CH CH132802D patent/CH132802A/en unknown
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