GB977227A - Acyl-propiolic acid esters and process for their manufacture - Google Patents
Acyl-propiolic acid esters and process for their manufactureInfo
- Publication number
- GB977227A GB977227A GB2610662A GB2610662A GB977227A GB 977227 A GB977227 A GB 977227A GB 2610662 A GB2610662 A GB 2610662A GB 2610662 A GB2610662 A GB 2610662A GB 977227 A GB977227 A GB 977227A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- substituted
- acids
- groups
- propiolic
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- -1 silver propiolic acid ester Chemical class 0.000 abstract 2
- KHRDXDOTSUZBMV-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-4,9,12-trioxododeca-2,10-diynoic acid Chemical class C(C)(C)(C)OC(C#CC(CCCCC(=O)C#CC(=O)O)=O)=O KHRDXDOTSUZBMV-UHFFFAOYSA-N 0.000 abstract 1
- ICPWFHKNYYRBSZ-UHFFFAOYSA-N 2-methoxypropanoic acid Chemical class COC(C)C(O)=O ICPWFHKNYYRBSZ-UHFFFAOYSA-N 0.000 abstract 1
- OYVCPHJJFPNOTH-UHFFFAOYSA-N 4-oxopent-2-ynoic acid Chemical compound CC(=O)C#CC(O)=O OYVCPHJJFPNOTH-UHFFFAOYSA-N 0.000 abstract 1
- KTJPPKKTODYILG-UHFFFAOYSA-N C(C(C)C)(=O)C#CC(=O)O Chemical compound C(C(C)C)(=O)C#CC(=O)O KTJPPKKTODYILG-UHFFFAOYSA-N 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical class OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acylpropiolic acid esters are prepared by reacting an acid halide of a carboxylic acid containing in the a -position at least one hydrogen atom with a silver propiolic acid ester <FORM:0977227/C1/1> where R1 represents a hydrocarbon group which may be substituted by one or more groups not capable of forming metal salts, in an organic solvent and in the absence of water. Compounds claimed are the acylpropiolic esters of formula <FORM:0977227/C1/2> in which <FORM:0977227/C1/3> represents the acyl radical or a carboxylic acid free from groups capable of reacting with silver ions and containing in the a -position at least one hydrogen atom, and R1 represents a hydrocarbon group containing at least two carbon atoms and which may be substituted by one or more groups not capable of forming metal salts, specifically acetylpropiolic acid-, isobutyrylpropiolic acid-, 3b -acetoxy -5a - etianoyl-propiolic acid-, crotonyl propiolic acid-, adipinyl-bis-propiolic acid-t-butyl esters, and their preparation is exemplified. The acid halide may be derived from acetic propionic, butyric, crotonic, stearic, palmitic, oleic, sebacic, adipic, glutaric or methoxypropionic acids, unsubstituted or substituted cyclohexane or cyclopentane carboxylic acids, cyclohexyl- or cyclopentyl-alkane carboxylic acids such as unsubstituted or substituted etianic, cholanic, norcolanic, bis-norcholanic acids or their 5a -isomers or the corresponding 18-nor or 19-nor compounds, pyrrolidine-, piperidine-, or tetrahydrofuran carboxylic acids, and other araliphatic or heterocyclic aliphatic acids, which may be substituted by hydroxyl, amino, nitro, alkyl, alkylene halogen groups. Specification 977,228 is referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH808461 | 1961-07-11 | ||
| CH738062 | 1962-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB977227A true GB977227A (en) | 1964-12-02 |
Family
ID=25701225
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5124663A Expired GB977228A (en) | 1961-07-11 | 1962-07-06 | Silver propiolic acid esters and process for their manufacture |
| GB2610662A Expired GB977227A (en) | 1961-07-11 | 1962-07-06 | Acyl-propiolic acid esters and process for their manufacture |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5124663A Expired GB977228A (en) | 1961-07-11 | 1962-07-06 | Silver propiolic acid esters and process for their manufacture |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE620022A (en) |
| GB (2) | GB977228A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641801A (en) * | 2013-11-14 | 2014-03-19 | 博通维德（北京）生物科技有限公司 | Stearic acid-tetrahydrofuran-3,4-diester synthetic method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2797735A (en) * | 1953-03-05 | 1957-07-02 | Chrysler Corp | Seat structures and upholstery units therefor |
-
0
- BE BE620022D patent/BE620022A/xx unknown
-
1962
- 1962-07-06 GB GB5124663A patent/GB977228A/en not_active Expired
- 1962-07-06 GB GB2610662A patent/GB977227A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641801A (en) * | 2013-11-14 | 2014-03-19 | 博通维德（北京）生物科技有限公司 | Stearic acid-tetrahydrofuran-3,4-diester synthetic method |
Also Published As
| Publication number | Publication date |
|---|---|
| GB977228A (en) | 1964-12-02 |
| BE620022A (en) |
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