CS198169B2 - Způsob výroby derivátů kyseliny a-řenyipropianové - Google Patents
Způsob výroby derivátů kyseliny a-řenyipropianové Download PDFInfo
- Publication number
- CS198169B2 CS198169B2 CS466375A CS466375A CS198169B2 CS 198169 B2 CS198169 B2 CS 198169B2 CS 466375 A CS466375 A CS 466375A CS 466375 A CS466375 A CS 466375A CS 198169 B2 CS198169 B2 CS 198169B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- mixture
- water
- phenylpropionic acid
- acid
- alpha
- Prior art date
Links
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 claims description 9
- 229960002218 sodium chlorite Drugs 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- DMZVZANOMJGHKO-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(C(C)C=O)C=C1 DMZVZANOMJGHKO-UHFFFAOYSA-N 0.000 description 4
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910001923 silver oxide Inorganic materials 0.000 description 3
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical class O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- VGMCZELQCNPMQV-UHFFFAOYSA-N 2-(4-ethylphenyl)propanoic acid Chemical compound CCC1=CC=C(C(C)C(O)=O)C=C1 VGMCZELQCNPMQV-UHFFFAOYSA-N 0.000 description 1
- PJIURQRCQMEQNR-UHFFFAOYSA-N 2-[4-(cyclopropylmethyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1CC1CC1 PJIURQRCQMEQNR-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL17235774A PL93841B1 (enrdf_load_html_response) | 1974-07-01 | 1974-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS198169B2 true CS198169B2 (cs) | 1980-05-30 |
Family
ID=19968031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS466375A CS198169B2 (cs) | 1974-07-01 | 1975-07-01 | Způsob výroby derivátů kyseliny a-řenyipropianové |
Country Status (7)
| Country | Link |
|---|---|
| CS (1) | CS198169B2 (enrdf_load_html_response) |
| DD (1) | DD118605A5 (enrdf_load_html_response) |
| HU (1) | HU172065B (enrdf_load_html_response) |
| PL (1) | PL93841B1 (enrdf_load_html_response) |
| RO (1) | RO67241A (enrdf_load_html_response) |
| SU (1) | SU691074A3 (enrdf_load_html_response) |
| YU (1) | YU36480B (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987000519A1 (en) * | 1985-07-12 | 1987-01-29 | The Upjohn Company | Chemical compounds comrpising substituted phenylrings |
-
1974
- 1974-07-01 PL PL17235774A patent/PL93841B1/pl unknown
-
1975
- 1975-06-27 YU YU166275A patent/YU36480B/xx unknown
- 1975-06-30 SU SU752149407A patent/SU691074A3/ru active
- 1975-07-01 DD DD18700975A patent/DD118605A5/xx unknown
- 1975-07-01 HU HU75PO00000592A patent/HU172065B/hu not_active IP Right Cessation
- 1975-07-01 RO RO7582723A patent/RO67241A/ro unknown
- 1975-07-01 CS CS466375A patent/CS198169B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL93841B1 (enrdf_load_html_response) | 1977-06-30 |
| YU36480B (en) | 1984-02-29 |
| DD118605A5 (enrdf_load_html_response) | 1976-03-12 |
| RO67241A (ro) | 1980-04-15 |
| YU166275A (en) | 1982-02-25 |
| SU691074A3 (ru) | 1979-10-05 |
| HU172065B (hu) | 1978-05-28 |
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