GB596095A - A process for the manufacture of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethylenes and of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethanes - Google Patents
A process for the manufacture of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethylenes and of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethanesInfo
- Publication number
- GB596095A GB596095A GB1843345A GB1843345A GB596095A GB 596095 A GB596095 A GB 596095A GB 1843345 A GB1843345 A GB 1843345A GB 1843345 A GB1843345 A GB 1843345A GB 596095 A GB596095 A GB 596095A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pinacoline
- alcohol
- lower alkyl
- dihydroxydiphenyl
- treating
- 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
- 125000005192 alkyl ethylene group Chemical group 0.000 title abstract 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N 4,4'-Biphenol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 title 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- DFOXKPDFWGNLJU-UHFFFAOYSA-N Pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 abstract 5
- 230000000875 corresponding Effects 0.000 abstract 5
- -1 alkyl ketone Chemical class 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 229960000583 Acetic Acid Drugs 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- IVDFJHOHABJVEH-UHFFFAOYSA-N Pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000012362 glacial acetic acid Substances 0.000 abstract 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- PJGSXYOJTGTZAV-UHFFFAOYSA-N Pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000012024 dehydrating agents Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 abstract 2
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 2
- RARSHUDCJQSEFJ-UHFFFAOYSA-N Paroxypropione Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000001076 estrogenic Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 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
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/003—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by hydrogenation of an unsaturated part
-
- 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
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- 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
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
a : b - (p : p1 - Dihydroxydiphenyl) - a : b - di - lower alkyl ethylenes are obtained by converting a p-hydroxy-phenyl-lower alkyl ketone by treating with sodium amalgam in alkaline medium into the corresponding pinacol, treating the pinacol with a dehydrating agent to obtain the corresponding pinacoline, treating this latter with an alkali metal and an alcohol to obtain the corresponding pinacoline alcohol and reacting the pinacoline alcohol with a dehydrating agent, particularly a mineral acid. a : b - (p : p1 - Dihydroxydiphenyl) - a : b - di - lower alkyl ethanes are obtained (a) by hydrogenating the corresponding ethylenic compound obtained as above; (b) by converting a p-hydroxy-phenyl-lower alkyl ketone as above into the pinacoline alcohol, and treating this with hydrogen iodide, advantageously in conjunction with red phosphorus. In all cases, the expression "lower alkyl" represents an alkyl group containing not more than five carbon atoms. Suitable agents for dehydrating the pinacoline alcohols are halogen hydracids, especially hydrogen chloride or bromide. Both the saturated and unsaturated products are oestrogenic. In examples: (1) p-hydroxypropiophenone, in aqueous caustic soda, is shaken with sodium amalgam and the free pinacol, obtained by adding glacial acetic acid, is treated, in ether, with gaseous hydrogen chloride, the resulting pinacoline being reduced to the corresponding pinacoline alcohol by sodium and alcohol, prior to saturation, in ether, with hydrogen chloride to obtain a : b -(p : p1 - dihydroxydiphenyl) - a : b - diethyl - ethylene; (2) the pinacoline alcohol of (1) is heated in glacial acetic acid with hydriodic acid and red phosphorus to obtain a : b -(p : p1-dihydroxydiphenyl) - a : b - diethylethane; (3) the product of (1) is reduced with hydrogen iodide and red phosphorus in glacial acetic acid to obtain the product of (2).
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB596095A true GB596095A (en) | 1947-12-29 |
Family
ID=1733911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1843345A Expired GB596095A (en) | 1945-07-18 | A process for the manufacture of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethylenes and of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethanes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB596095A (en) |
-
1945
- 1945-07-18 GB GB1843345A patent/GB596095A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB596095A (en) | A process for the manufacture of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethylenes and of ª‡, ª‰-(p, p-dihydroxy-diphenyl)-ª‡, ª‰-di-lower alkyl-ethanes | |
| GB592827A (en) | Improvements in or relating to the manufacture of phenoxyalkylcarboxylic compounds | |
| GB918929A (en) | Improvements in or relating to process for the manufacture of therapeutic useful preparations of iron | |
| GB1109133A (en) | Dihydropyran ethers and unsaturated aliphatic ketoethers | |
| GB737606A (en) | Preparation of aldehydopentadecanoic acid and dialdehydotetradecane | |
| GB673442A (en) | New ether and process for the production thereof | |
| SU129651A1 (en) | Method for preparing hydratronic alcohol | |
| GB585316A (en) | Improvements in or relating to the purification of capryl alcohol | |
| GB891447A (en) | Light and heat stable cellulose fibrous products and process for making them | |
| GB1049034A (en) | New compounds of the coenzyme q type | |
| GB772966A (en) | Preparation of 2,4,5-trichlorophenoxyacetic acid | |
| GB625281A (en) | Prepaartion of di(chlorethyl)benzene and of divinyl benzene | |
| GB753222A (en) | Production of pentadecanedioic acid | |
| GB697977A (en) | Process for the manufacture of hydroxy-indazoles | |
| GB624568A (en) | Process for the manufacture of thioglycollic acid or its salts | |
| GB307985A (en) | Improvements relating to the recuperation of hydrochloric acid gas from aqueous hydrochloric acid | |
| GB900564A (en) | Improvements in or relating to the preparation of aromatic alcohols | |
| GB756006A (en) | Process for the preparation of alkoxy-tetrahydrofuranes | |
| GB610859A (en) | A process for the manufacture of an antibacterial substance | |
| GB609803A (en) | A process for the preparation of 2-methyl-2.3-di-halogen-tetrahydrofuranes and their conversion to vitamin b and the like | |
| GB469921A (en) | Process for the manufacture of trialkylacetamides with saturated alkyl groups | |
| GB495050A (en) | Process for the production of 2-keto-ª•-gulonic acid | |
| GB585299A (en) | Improvements in or relating to the manufacture of aldol | |
| GB632805A (en) | Process for the production of compounds reducing the prothrombin level in the blood | |
| GB762991A (en) | Improvements in or relating to the manufacture of n:n -dibenzylethylenediamine |