GB720251A - Improvements relating to o-aminophenols - Google Patents
Improvements relating to o-aminophenolsInfo
- Publication number
- GB720251A GB720251A GB31979/52A GB3197952A GB720251A GB 720251 A GB720251 A GB 720251A GB 31979/52 A GB31979/52 A GB 31979/52A GB 3197952 A GB3197952 A GB 3197952A GB 720251 A GB720251 A GB 720251A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloromethyl
- sulphone
- nitrobenzene
- chloro
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 title 1
- -1 4-hydroxy-3-aminobenzene-1-chloromethyl sulphone Chemical compound 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 abstract 1
- QBLQHDHWTVMHRH-UHFFFAOYSA-N 4-bromobenzenesulfinic acid Chemical compound OS(=O)C1=CC=C(Br)C=C1 QBLQHDHWTVMHRH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229960005215 dichloroacetic acid Drugs 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 4-hydroxy-3-aminobenzene-1-chloromethyl sulphone. The compound is produced by replacing the nuclear-bound halogen atom in a 4-halogen-3-nitrobenzene-1-chloromethyl sulphone by a hydroxyl group by heating with aqueous alkali and reducing the nitro group to an amino group. In the example: 4-Chloro-3-nitrobenzene-1-chloromethyl sulphone, obtained by treating 4-chlorobenzene-1-chloromethyl sulphone dissolved in concentrated sulphuric acid with a mixture of nitric and sulphuric acids, is heated with aqueous sodium hydroxide to form 4-hydroxy - 3 - nitrobenzene - 1 - chloromethyl sulphlne which is reduced by heating with iron and aqueous hydrochloric acid to 4-hydroxy-3-aminobenzene-1-chloromethyl sulphone. 4-Bromobenzene-1-chloromethyl sulphone may be employed as starting material in a similar process. 4 - Chloro - or 4 - bromo - benzene - 1 - chloromethyl sulphone can be obtained by heating the sodium salt of 4-chloro- or 4-bromobenzene sulphinic acid with the sodium salt of dichloroacetic acid in aqueous solution when carbon dioxide is split off.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH720251X | 1951-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB720251A true GB720251A (en) | 1954-12-15 |
Family
ID=4531481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31979/52A Expired GB720251A (en) | 1951-12-21 | 1952-12-17 | Improvements relating to o-aminophenols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB720251A (en) |
-
1952
- 1952-12-17 GB GB31979/52A patent/GB720251A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB662800A (en) | Improvements in or relating to the preparation of salts of cyclohexylsulphamic acid | |
| GB720251A (en) | Improvements relating to o-aminophenols | |
| GB934292A (en) | Process for the preparation of heterocyclic compounds | |
| GB568850A (en) | Guanidine derivatives | |
| GB597810A (en) | Improvements in or relating to derivatives of diphenyl | |
| GB633459A (en) | A process for the manufacture of n-(p-arsenosobenzyl)-glycine-amide and salts thereof | |
| GB597809A (en) | Improvements in or relating to derivatives of diphenyl | |
| GB636333A (en) | Improvements in and relating to the manufacture of aromatic amino carboxylic acids | |
| GB624568A (en) | Process for the manufacture of thioglycollic acid or its salts | |
| GB771484A (en) | Preparation of -ß-aminomethyltropolone | |
| GB601184A (en) | Improvements in or relating to the preparation of alkyl acylaminocyanoacetates | |
| GB647209A (en) | 4-substituted-1-amino-ar-tetrahydro-2-naphthols | |
| GB596230A (en) | Improvements in or relating to the production of quinolinic acid and metal salts thereof | |
| GB396100A (en) | Process for the manufacture of 2-alkyl-aminobenzene-1-carboxylic acid-4-sulphonic acids | |
| GB710151A (en) | Process for the manufacture of n-acylated amino aryl sulphonamides | |
| GB899584A (en) | Benzenesulphonamides | |
| GB632773A (en) | Improvements in and relating to the preparation of compounds derived from polynuclear organic acids and phenols | |
| GB655708A (en) | A method of producing tetryl | |
| GB605973A (en) | Improvements in methods for the production of salts of chlorethane sulphonic acid | |
| GB606198A (en) | Improvements in and relating to thiophene compounds and processes of preparing the same | |
| GB583221A (en) | Improvements in the manufacture of mepacrine hydrochloride | |
| GB668567A (en) | Improvements in or relating to a method of preparing a stable theophylline composition and the product resulting therefrom | |
| GB599688A (en) | Improvements in or relating to the production of pyrazine derivatives | |
| GB470462A (en) | Process for the manufacture of derivatives of aminobenzene sulphonic acid amides | |
| GB435113A (en) | The manufacture of organic disulphides |