GB478902A - A process for the preparation of a condensation product of iodoform and guaiacol - Google Patents
A process for the preparation of a condensation product of iodoform and guaiacolInfo
- Publication number
- GB478902A GB478902A GB29212/36A GB2921236A GB478902A GB 478902 A GB478902 A GB 478902A GB 29212/36 A GB29212/36 A GB 29212/36A GB 2921236 A GB2921236 A GB 2921236A GB 478902 A GB478902 A GB 478902A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodoform
- guaiacol
- proportions
- weight
- extracted
- 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
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 title abstract 12
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 title abstract 12
- 229960001867 guaiacol Drugs 0.000 title abstract 6
- 239000007859 condensation product Substances 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 239000000243 solution Substances 0.000 abstract 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000012262 resinous product Substances 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 238000001256 steam distillation Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Guaiacol is heated with iodoform, preferably in the proportions of 1,2 : 1 by weight, and the bye-products and unchanged starting materials removed by distillation or extraction with solvents. The product, which possesses therapeutic properties, may be purified by treatment with aqueous solutions of weak alkalies, preferably alkali carbonates and bicarbonates and in order of increasing alkalinity, and further purified by extraction with aqueous alkali bisulphite. According to the examples: (1) guaiacol and iodoform in the proportions by weight of 2,5 : 1 are heated together for some days at 105 DEG C. until no more methyl iodide is evolved and then distilled in vacuo; (2) guaiacol and iodoform in the proportions by weight of 1,2 : 1 are condensed as in (1) and the mass subjected to distillation in vacuo, steam distillation or solvent extraction; (3) the product of (1) or (2), if desired after dissolution in acetone, is heated with sodium carbonate solution with exclusion of air and acid then added to precipitate the purified compound ; alternatively, the starting material is extracted at ordinary temperature first with sodium bicarbonate solution and then with sodium carbonate solution and the solutions acidified, or the starting material is extracted in a nitrogen atmosphere with caustic soda solution and carbon dioxide then passed into the filtrate to separate the purified compound; (4) the product of (3) is twice extracted with sodium bisulphite solution and the precipitate formed on acidification extracted with ethyl acetate. The Specification as open to inspection under Sect. 91 also contains examples which describe the interaction by prolonged heat treatment of iodoform and guaiacol in the proportions by weight of 1 : 5 and 1 : 1 respectively. A further example is given according to which the reaction mixture of iodoform and guaiacol in the proportions by weight of 1 : 1,2, after prlonged heating is stirred into hot toluene, when a resinous product separates out. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU478902X | 1935-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB478902A true GB478902A (en) | 1938-01-27 |
Family
ID=10979295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29212/36A Expired GB478902A (en) | 1935-11-06 | 1936-10-27 | A process for the preparation of a condensation product of iodoform and guaiacol |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB478902A (en) |
-
1936
- 1936-10-27 GB GB29212/36A patent/GB478902A/en not_active Expired
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