GB890603A - Preparation of acetylenic alcohols - Google Patents
Preparation of acetylenic alcoholsInfo
- Publication number
- GB890603A GB890603A GB17599/60A GB1759960A GB890603A GB 890603 A GB890603 A GB 890603A GB 17599/60 A GB17599/60 A GB 17599/60A GB 1759960 A GB1759960 A GB 1759960A GB 890603 A GB890603 A GB 890603A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- radical
- pentyn
- butyn
- formula
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acetylenic alcohols are prepared by reacting an acetylenic hydrocarbon of formula CHCR, in which R represents hydrogen or a hydrocarbon radical, with a catalytic quantity of an alkali metal hydroxide and an aldehyde or ketone at a temperature of at least -10 DEG C. and at superatmospheric pressure in the presence of liquid ammonia, and subsequently hydrolysing the reaction mixture. The reaction is preferably carried out at a temperature from -10 DEG C. to 60 DEG C. and a pressure of 25-800 p.s.i.g. The aldehyde or ketone preferably has the formula R1COR2 in which R1 and R2 are the same or different and each is hydrogen, an alkyl radical of 1-20 carbon atoms, a cycloalkyl radical of 3-10 carbon atoms, an aryl radical of 6-12 carbon atoms, a hydroxyalkyl radical of 1-20 carbon atoms, a hydroxycycloalkyl radical of 3-10 carbon atoms, an alkoxyalkyl radical of 2-20 carbon atoms, or an alkoxyalkyl radical of 4-20 carbon atoms, or in which R1 and R2 are joined to form together with the shared carbon atom a cycloalkyl radical of 6-12 carbon atoms. The alkali metal hydroxide used is preferably of at least 90% purity, is finely divided, i.e. of 80-100 mesh or higher, and contains less than 5% of water. The hydrolysis is preferably carried out with water in the presence of an organic solvent, e.g. an ether of formula R3OR4 in which R3 and R4 are alkyl radicals having 1-6 carbon atoms. Examples are given of the preparation of 5-methyl-1-butyn-3-ol, 3-methyl-1-pentyn-3-ol, 3,5-dimethyl-1-hexyn-3-ol, 3-ethyl-1-pentyn-3-ol 1-ethynyl-cyclohexanol-1, 3-ethyl-1-heptyn-3-ol, 3-phenyl-1-butyn-3-ol, 1-hexyn-3-ol, 1-pentyn-3-ol, isodecynol and 1-butyn-3-ol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH890603X | 1959-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB890603A true GB890603A (en) | 1962-03-07 |
Family
ID=4545726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17599/60A Expired GB890603A (en) | 1959-05-20 | 1960-05-18 | Preparation of acetylenic alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB890603A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3379777A (en) * | 1964-04-02 | 1968-04-23 | Hoffmann La Roche | Acetylenic carbinols |
| WO2022114942A1 (en) * | 2020-11-27 | 2022-06-02 | Нао "Атырауский Университет Нефти И Газа Имени С.Утебаева" | Octane-increasing additive for gasoline |
| CN115710159A (en) * | 2022-12-06 | 2023-02-24 | 辽宁鑫隆科技有限公司 | Method for purifying 1-ethynyl cyclohexanol by melt crystallization method |
-
1960
- 1960-05-18 GB GB17599/60A patent/GB890603A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3379777A (en) * | 1964-04-02 | 1968-04-23 | Hoffmann La Roche | Acetylenic carbinols |
| WO2022114942A1 (en) * | 2020-11-27 | 2022-06-02 | Нао "Атырауский Университет Нефти И Газа Имени С.Утебаева" | Octane-increasing additive for gasoline |
| CN115710159A (en) * | 2022-12-06 | 2023-02-24 | 辽宁鑫隆科技有限公司 | Method for purifying 1-ethynyl cyclohexanol by melt crystallization method |
| CN115710159B (en) * | 2022-12-06 | 2023-11-21 | 辽宁鑫隆科技有限公司 | Method for purifying 1-ethynyl cyclohexanol by using melt crystallization method |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB890603A (en) | Preparation of acetylenic alcohols | |
| GB1260643A (en) | Process for the preparation of quaternary ammonium compounds | |
| GB948175A (en) | Process for the production of 2, 4-diamino-6-trichloromethyl-úË-triazines | |
| US3366634A (en) | Preparation of tetrahydropyrimidines | |
| GB1008175A (en) | A process for the hydrogenation of unsaturated halogenated organic compounds | |
| GB1122034A (en) | Process for the preparation of azines | |
| GB1094925A (en) | Anthraquinone dyestuffs containing aralkylamino groups | |
| US3002977A (en) | Ethyl 2-(2-cyclohexenylthio)-4-thiazolecarboxylate | |
| GB951435A (en) | Production of acyl-alkyl-phenols | |
| GB1101624A (en) | A process for the manufacture of acetylenic carbinols | |
| GB1067345A (en) | Novel steroid compounds, processes for preparing them and compositions containing them | |
| GB938646A (en) | New piperazine derivatives | |
| GB1049769A (en) | Organic compounds containing an isocyclic and a heterocyclic non-aromatic ring and aprocess for the production of these compounds | |
| GB671412A (en) | Production of keto compounds | |
| GB1104323A (en) | 3-phenylpyrrole derivatives and process for preparing the same | |
| GB1067782A (en) | Aldimines | |
| GB902014A (en) | A process for the preparation of tertiary acetylenic alcohols | |
| GB942877A (en) | Improvements in or relating to a thiaxanthene derivative | |
| GB775723A (en) | Process for the production of allyl substituted acetylene compounds | |
| GB1041052A (en) | Process for the production of alkynols | |
| GB899691A (en) | Process for the production of acetic acid from methanol and carbon monoxide | |
| ES240537A1 (en) | Procedure for the production of finilciclohexilamine compounds. (Machine-translation by Google Translate, not legally binding) | |
| GB836289A (en) | Two-stage method for preparing carbon-substituted piperazines | |
| GB814665A (en) | Ethylene polymerisation | |
| GB908504A (en) | Process for the production of new glycols |