DE1929731A1 - Verfahren zur Herstellung von 2,3-Dichlor4-(2'-Methylenbutyryl)-Phenoxyessigsaeure - Google Patents
Verfahren zur Herstellung von 2,3-Dichlor4-(2'-Methylenbutyryl)-PhenoxyessigsaeureInfo
- Publication number
- DE1929731A1 DE1929731A1 DE19691929731 DE1929731A DE1929731A1 DE 1929731 A1 DE1929731 A1 DE 1929731A1 DE 19691929731 DE19691929731 DE 19691929731 DE 1929731 A DE1929731 A DE 1929731A DE 1929731 A1 DE1929731 A1 DE 1929731A1
- Authority
- DE
- Germany
- Prior art keywords
- dichloro
- compound
- mixture
- phenoxyacetic acid
- formaldehyde
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 title claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- -1 oxo compound Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract description 3
- 239000002934 diuretic Substances 0.000 abstract description 3
- 238000010992 reflux Methods 0.000 abstract description 3
- 230000003216 chloruretic effect Effects 0.000 abstract description 2
- 230000001882 diuretic effect Effects 0.000 abstract description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000155 melt Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FQAYODYTZPXLRH-UHFFFAOYSA-N 2-(4-butanoyl-2,3-dichlorophenoxy)acetic acid Chemical compound CCCC(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl FQAYODYTZPXLRH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- XWYGGAJWANYRPA-UHFFFAOYSA-N methyl 2-(4-butanoyl-2,3-dichlorophenoxy)acetate Chemical compound CCCC(=O)C1=C(Cl)C(Cl)=C(OCC(=O)OC)C=C1 XWYGGAJWANYRPA-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000007281 aminoalkylation reaction Methods 0.000 description 1
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001534 | 1968-06-21 | ||
| HUEE001534 | 1968-06-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1929731A1 true DE1929731A1 (de) | 1970-01-08 |
| DE1929731C DE1929731C (enrdf_load_stackoverflow) | 1973-04-26 |
Family
ID=10995260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691929731 Granted DE1929731A1 (de) | 1968-06-21 | 1969-06-12 | Verfahren zur Herstellung von 2,3-Dichlor4-(2'-Methylenbutyryl)-Phenoxyessigsaeure |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT293364B (enrdf_load_stackoverflow) |
| DE (1) | DE1929731A1 (enrdf_load_stackoverflow) |
| DK (1) | DK131563B (enrdf_load_stackoverflow) |
| NL (1) | NL142147B (enrdf_load_stackoverflow) |
| SE (1) | SE349293B (enrdf_load_stackoverflow) |
| YU (1) | YU32018B (enrdf_load_stackoverflow) |
-
1969
- 1969-06-12 AT AT560469A patent/AT293364B/de not_active IP Right Cessation
- 1969-06-12 DE DE19691929731 patent/DE1929731A1/de active Granted
- 1969-06-18 SE SE870469A patent/SE349293B/xx unknown
- 1969-06-18 YU YU154969A patent/YU32018B/xx unknown
- 1969-06-19 DK DK329369A patent/DK131563B/da not_active IP Right Cessation
- 1969-06-20 NL NL6909501A patent/NL142147B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT293364B (de) | 1971-10-11 |
| NL142147B (nl) | 1974-05-15 |
| DK131563C (enrdf_load_stackoverflow) | 1975-12-29 |
| DK131563B (da) | 1975-08-04 |
| YU154969A (en) | 1973-08-31 |
| YU32018B (en) | 1974-02-28 |
| NL6909501A (enrdf_load_stackoverflow) | 1969-12-23 |
| SE349293B (enrdf_load_stackoverflow) | 1972-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |