GB790842A - Substituted cyclopentenes and methods of preparing same - Google Patents
Substituted cyclopentenes and methods of preparing sameInfo
- Publication number
- GB790842A GB790842A GB2053956A GB2053956A GB790842A GB 790842 A GB790842 A GB 790842A GB 2053956 A GB2053956 A GB 2053956A GB 2053956 A GB2053956 A GB 2053956A GB 790842 A GB790842 A GB 790842A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclopentenyl
- alkali metal
- ketobutyrate
- ethyl
- cyclopenten
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/242—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 2-(2-cyclopentenyl)-3 - methyl - 2 - cyclopenten - 4 - ol - 1 - one represented by the formula: <FORM:0790842/IV (b)/1> and (a) a process for preparing ethyl 4-(2-cyclopentenyl)-3-ketobutyrate which comprises the steps of reacting cyclopentadiene with hydrogen chloride to produce 2-cyclopentenyl chloride, heating an alkali metal derivative of acetoacetic ester with the 2-cyclopentenyl chloride to produce ethyl 2-(2-cyclopentenyl)-3-ketobutyrate, subjecting the 2-(2-cyclopentenyl)3-ketobutyrate to ketonic hydrolysis in the presence of an aqueous solution of an alkyl metal hydroxide, acidifying the reaction mixture with aqueous sulphuric acid, then distilling to form 2-cyclopentenyl acetone and heating the 2-cyclopentenyl acetone with diethyl carbonate in the presence of an alkali metal alcoholate to form ethyl 4 - (2 - cyclopentenyl) - 3 - ketobutyrate; (b) a process in which the ethyl 4-(2-cyclopentenyl)-3-ketobutyrate prepared by the latter process is converted to the alkali metal salt of 4-(2 - cyclopentenyl) - 3 - ketobutyric acid by reaction with aqueous alkali metal hydroxide; (e) a process in which the alkali metal salt prepared by the latter process is reacted with an aqueous solution of pyruvic aldehyde to form 6-(2 - cyclopentenyl) - 3 - hydroxyhexane - 2,5-dione; and (d) a process in which the 6-(2-cyclopentenyl) - 3 - hydroxyhexane - 2,5 - dione prepared by the latter process is treated with a substantially 2 per cent by weight aqueous solution of alkali metal hydroxide to convert it to 2 - (2 - cyclopentenyl) - 3 - methyl - 2 - cyclopenten - 4 - ol - 1 - one. In the example 2 - (2 - cyclopentenyl) - 3 - methyl - 2 - cyclopenten - 4 - ol - 1 - one is obtained by a process comprising the above steps and is purified by conversion to the semicarbazone followed by hydrolysis.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2053956A GB790842A (en) | 1954-06-22 | 1954-06-22 | Substituted cyclopentenes and methods of preparing same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2053956A GB790842A (en) | 1954-06-22 | 1954-06-22 | Substituted cyclopentenes and methods of preparing same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB790842A true GB790842A (en) | 1958-02-19 |
Family
ID=10147562
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2053956A Expired GB790842A (en) | 1954-06-22 | 1954-06-22 | Substituted cyclopentenes and methods of preparing same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB790842A (en) |
-
1954
- 1954-06-22 GB GB2053956A patent/GB790842A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1005897A (en) | Process for the preparation of cyclopropanecarboxylic acid derivatives and intermediates useful therein | |
GB1205050A (en) | Process for preparing bicyclopentadecenones | |
GB799269A (en) | Production of intermediates for the synthesis of reserpine and related compounds | |
GB1264592A (en) | ||
GB1155022A (en) | Hydroxymethane Carboxylic Acid Esters and process for their manufacture | |
GB790842A (en) | Substituted cyclopentenes and methods of preparing same | |
GB953775A (en) | Processes for the preparation of sorbic acid and alkyl esters of sorbic acid | |
US3287372A (en) | Process and intermediates for manufacture of 2-(dialkylmethyl)-5-alkyl-2-cyclohexen-1-ones | |
GB655864A (en) | Improvements in and relating to the condensation of alcohols | |
GB646828A (en) | Process for preparing artificial oestrogenic compounds and products obtained thereby | |
GB1030491A (en) | Trans-7-hydroxy-hept-2-enoic acid | |
US3246038A (en) | Process for the production of 4-[2', 6', 6'-trimethylcyclohexen-(1')-yl]-2-methylbuten-(3)-al | |
GB788302A (en) | The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom | |
US2979529A (en) | Production of dicyclopropyl ketones and 1, 7-dihalo-4-heptanones | |
US2786872A (en) | Method for the conversion of nitriles to aldehydes | |
GB577481A (en) | Manufacture of fluoroacetic acids and alkali metal salts thereof | |
US2600387A (en) | Carboxyalkylation of ketonic compounds | |
GB785086A (en) | Novel unsaturated ketones and a process for the manufacture thereof | |
US4026911A (en) | Process for the preparation of ketoalkynoic acids and use of the process in an improved synthesis of 2-(substituted)-cyclo-pentane-1,3,4-triones | |
SU550389A1 (en) | The method of obtaining six-membered heterocyclic aldehydes | |
SU1594162A1 (en) | Method of producing 1-substituted cyclopropanes | |
GB787061A (en) | Process for producing n-methyl--a-phenylsuccinimide | |
GB784891A (en) | Novel unsaturated ketones and a process for the manufacture thereof | |
GB695529A (en) | Process for the production of crystalline vanillyl amides | |
GB948752A (en) | A process for the manufacture of unsaturated ketones |