DE2244012C3 - Verfahren zur Herstellung von Alkoxyacetessigestern - Google Patents
Verfahren zur Herstellung von AlkoxyacetessigesternInfo
- Publication number
- DE2244012C3 DE2244012C3 DE19722244012 DE2244012A DE2244012C3 DE 2244012 C3 DE2244012 C3 DE 2244012C3 DE 19722244012 DE19722244012 DE 19722244012 DE 2244012 A DE2244012 A DE 2244012A DE 2244012 C3 DE2244012 C3 DE 2244012C3
- Authority
- DE
- Germany
- Prior art keywords
- ester
- alkoxyacetoacetic
- esters
- preparation
- bromoacetoacetic
- 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
- 150000002148 esters Chemical class 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 aliphatic alcohols Chemical class 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- QGBPKJFJAVDUNC-UHFFFAOYSA-N methyl 4-methoxy-3-oxobutanoate Chemical compound COCC(=O)CC(=O)OC QGBPKJFJAVDUNC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- NGGGZUAEOKRHMA-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoic acid Chemical compound CC(C)(C)OC(=O)CC(O)=O NGGGZUAEOKRHMA-UHFFFAOYSA-N 0.000 description 1
- GSMODZOCMUQSRT-UHFFFAOYSA-N 4-ethoxy-3-oxobutanoic acid Chemical compound CCOCC(=O)CC(O)=O GSMODZOCMUQSRT-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
- KNFXXAGQEUUZAZ-UHFFFAOYSA-N ethyl ethaneperoxoate Chemical compound CCOOC(C)=O KNFXXAGQEUUZAZ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QVBGSRKQOYZMLR-UHFFFAOYSA-N octyl 4-chloro-3-oxobutanoate Chemical compound CCCCCCCCOC(=O)CC(=O)CCl QVBGSRKQOYZMLR-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ASOLRMVAIXDZPW-UHFFFAOYSA-N propan-2-yl 3-oxo-4-propan-2-yloxybutanoate Chemical compound C(C)(C)OC(CC(=O)COC(C)C)=O ASOLRMVAIXDZPW-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- KRZQYDMOEZDDGE-UHFFFAOYSA-N sodium;octan-1-olate Chemical compound [Na+].CCCCCCCC[O-] KRZQYDMOEZDDGE-UHFFFAOYSA-N 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C69/67—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 saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C07C69/72—Acetoacetic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1327771A CH562191A5 (enExample) | 1971-09-10 | 1971-09-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2244012A1 DE2244012A1 (de) | 1973-03-15 |
| DE2244012B2 DE2244012B2 (de) | 1981-06-25 |
| DE2244012C3 true DE2244012C3 (de) | 1982-02-25 |
Family
ID=4390993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722244012 Expired DE2244012C3 (de) | 1971-09-10 | 1972-09-07 | Verfahren zur Herstellung von Alkoxyacetessigestern |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5318485B2 (enExample) |
| AT (1) | AT317165B (enExample) |
| BE (1) | BE788516A (enExample) |
| CA (1) | CA1003434A (enExample) |
| CH (1) | CH562191A5 (enExample) |
| CS (1) | CS158734B2 (enExample) |
| DD (1) | DD99157A5 (enExample) |
| DE (1) | DE2244012C3 (enExample) |
| FR (1) | FR2152722A1 (enExample) |
| IT (1) | IT965273B (enExample) |
| LU (1) | LU66030A1 (enExample) |
| NL (1) | NL178866C (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3263545D1 (en) * | 1981-10-01 | 1985-06-20 | Lonza Ag | Process for the preparation of 4-alkoxy-acetoacetic-acid esters |
| EP0076378B1 (de) * | 1981-10-01 | 1985-01-02 | Lonza Ag | Verfahren zur Herstellung von 4-Alkoxyacetessigestern |
| WO1987003287A2 (en) * | 1985-11-20 | 1987-06-04 | L. Givaudan & Cie Societe Anonyme | PROCESS FOR PREPARING alpha-HYDROXY CARBONYL COMPOUNDS |
| BR112015014714B1 (pt) | 2012-12-21 | 2018-12-26 | Gilead Sciences, Inc. | compostos carbamoilpiridona policíclicos, composição farmacêutica que os compreende e seu uso farmacêutico |
| NO2865735T3 (enExample) | 2013-07-12 | 2018-07-21 | ||
| AU2014286993B2 (en) | 2013-07-12 | 2018-10-25 | Gilead Sciences, Inc. | Polycyclic-carbamoylpyridone compounds and their use for the treatment of HIV infections |
| TWI744723B (zh) | 2014-06-20 | 2021-11-01 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| NO2717902T3 (enExample) | 2014-06-20 | 2018-06-23 | ||
| TW201613936A (en) | 2014-06-20 | 2016-04-16 | Gilead Sciences Inc | Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide |
-
0
- BE BE788516D patent/BE788516A/xx not_active IP Right Cessation
-
1971
- 1971-09-10 CH CH1327771A patent/CH562191A5/xx not_active IP Right Cessation
-
1972
- 1972-09-07 DE DE19722244012 patent/DE2244012C3/de not_active Expired
- 1972-09-07 FR FR7231729A patent/FR2152722A1/fr active Granted
- 1972-09-07 NL NL7212180A patent/NL178866C/xx not_active IP Right Cessation
- 1972-09-07 JP JP8920272A patent/JPS5318485B2/ja not_active Expired
- 1972-09-08 IT IT5263172A patent/IT965273B/it active
- 1972-09-08 AT AT774172A patent/AT317165B/de not_active IP Right Cessation
- 1972-09-08 CA CA151,264A patent/CA1003434A/en not_active Expired
- 1972-09-08 DD DD16555972A patent/DD99157A5/xx unknown
- 1972-09-08 CS CS616272A patent/CS158734B2/cs unknown
- 1972-09-08 LU LU66030D patent/LU66030A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU430544A3 (ru) | 1974-05-30 |
| JPS5318485B2 (enExample) | 1978-06-15 |
| DE2244012A1 (de) | 1973-03-15 |
| AT317165B (de) | 1974-08-12 |
| BE788516A (fr) | 1973-03-07 |
| NL178866C (nl) | 1986-06-02 |
| JPS4834819A (enExample) | 1973-05-22 |
| FR2152722A1 (en) | 1973-04-27 |
| CS158734B2 (enExample) | 1974-11-25 |
| CH562191A5 (enExample) | 1975-05-30 |
| CA1003434A (en) | 1977-01-11 |
| LU66030A1 (enExample) | 1973-03-12 |
| DD99157A5 (enExample) | 1973-07-20 |
| IT965273B (it) | 1974-01-31 |
| DE2244012B2 (de) | 1981-06-25 |
| NL7212180A (enExample) | 1973-03-13 |
| FR2152722B1 (enExample) | 1978-02-10 |
| NL178866B (nl) | 1986-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS, D., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |