DE1951587B - - Google Patents
Info
- Publication number
- DE1951587B DE1951587B DE1951587B DE 1951587 B DE1951587 B DE 1951587B DE 1951587 B DE1951587 B DE 1951587B
- Authority
- DE
- Germany
- Prior art keywords
- compound
- trans
- cis
- base
- acetic acid
- 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.)
- Pending
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 28
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006317 isomerization reaction Methods 0.000 description 6
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- -1 ice compound Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2820854C2 (de) | Verfahren zur Herstellung von p-Hydroxyphenylessigsäure | |
| DE857042C (de) | Verfahren zur Umwandlung von Phenanthren in Anthracen | |
| DE1951587C (enExample) | ||
| DE2062928A1 (de) | Synthese von aliphatischen Amino und/oder Carboxy Verbindungen | |
| DE1951587B (enExample) | ||
| DE69409001T2 (de) | Chirale nitrile, ihre herstellung und ihre verwendung in der herstellung von verapamil und dessen analogen | |
| DE2831118A1 (de) | Verfahren zur herstellung von p-hydroxyphenylglycin und seiner n-alkyl- und n,n-dialkylderivate | |
| DE1287063B (de) | Verfahren zur Herstellung von 3, 4-Dichlorbuten-(1) | |
| DE69202177T2 (de) | Verfahren zur Herstellung von 3,3',4,4'-Tetramethyldiphenylmethan. | |
| DE952344C (de) | Verfarhen zur Monochlorierung des m-Xylols | |
| DE1468225A1 (de) | Verfahren zur Isomerisation von Xylolen | |
| CH601151A5 (en) | Alpha-ethynylbenzhydrols as inducers and inhibitors | |
| DE1951587A1 (de) | Verfahren zur Herstellung von 3t-Dimethyl-amino-4-phenyl- 4t-aethoxycarbonyl-delta?-cyclohexen aus 3c-Dimethylamino-4-phenyl-4c-aethoxycarbonyl-delta?-cyclohexen | |
| DE874913C (de) | Verfahren zur Herstellung von Aminothiolactonen | |
| DE1957259C3 (de) | Verfahren zur Herstellung von reinem 4-Amino- und 5-Aminoindan | |
| DE878943C (de) | Verfahren zur Herstellung ungesaettigter Nitrile | |
| EP0064651B1 (de) | Verfahren zur Isolierung von H-Säure und K-Säure | |
| EP0119463A1 (de) | Verfahren zur Trennung von substituierten Cyclopropancarbonsäureisomeren | |
| DE821787C (de) | Verfahren zur Gewinnung von Xylidinen | |
| DE2635401C3 (de) | Verfahren zur Herstellung von reinem 4-Aminoindan | |
| DE566034C (de) | Verfahren zur Herstellung von Dichloraethylen aus Tetrachloraethan | |
| DE942687C (de) | Verfahren zur Herstellung eines Gemisches von isomeren Dimethoxydecdienen | |
| DE1242592B (de) | Verfahren zur katalytischen Isomerisation von verzweigtkettigen Mono-Olefinen | |
| DE1903334A1 (de) | Verfahren zur Herstellung von para-Phenyl-phenolen | |
| WO1991001977A1 (de) | Verfahren zur herstellung von 2,6-dichlorchinoxalin |