PL86932B1 - - Google Patents
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- Publication number
- PL86932B1 PL86932B1 PL17353571A PL17353571A PL86932B1 PL 86932 B1 PL86932 B1 PL 86932B1 PL 17353571 A PL17353571 A PL 17353571A PL 17353571 A PL17353571 A PL 17353571A PL 86932 B1 PL86932 B1 PL 86932B1
- Authority
- PL
- Poland
- Prior art keywords
- propanol
- methylstyrene
- sulfuric acid
- boiled
- formula
- Prior art date
Links
- -1 3-phenoxyphenyl Chemical group 0.000 claims description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 3
- OINMNNGQSFIOQI-UHFFFAOYSA-N 1-butyl-4-prop-1-en-2-ylbenzene Chemical compound CCCCC1=CC=C(C(C)=C)C=C1 OINMNNGQSFIOQI-UHFFFAOYSA-N 0.000 claims description 2
- GPDATMGCLOLJBJ-UHFFFAOYSA-N 1-fluoro-4-(4-prop-1-en-2-ylphenyl)benzene Chemical compound CC(=C)C1=CC=C(C=C1)C1=CC=C(F)C=C1 GPDATMGCLOLJBJ-UHFFFAOYSA-N 0.000 claims description 2
- FXQJDGUGOZWQNL-UHFFFAOYSA-N 1-phenylsulfanyl-3-prop-1-en-2-ylbenzene Chemical compound C1(=CC=CC=C1)SC=1C=C(C=CC1)C(=C)C FXQJDGUGOZWQNL-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- QURXIISLVHJNGB-UHFFFAOYSA-N 2-(4-fluorophenyl)propan-2-ol Chemical compound CC(C)(O)C1=CC=C(F)C=C1 QURXIISLVHJNGB-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HDKGBYWBVZDOIW-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-4-ethenylbenzene Chemical compound CC(C)(C)CC1=CC=C(C=C)C=C1 HDKGBYWBVZDOIW-UHFFFAOYSA-N 0.000 description 1
- MXWQCJIFJKBTOT-UHFFFAOYSA-N 1-(2-methylpropyl)-4-prop-1-en-2-ylbenzene Chemical compound CC(C)CC1=CC=C(C(C)=C)C=C1 MXWQCJIFJKBTOT-UHFFFAOYSA-N 0.000 description 1
- MSDQNIRGPBARGC-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1CCCCC1 MSDQNIRGPBARGC-UHFFFAOYSA-N 0.000 description 1
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 description 1
- KEAGRYYGYWZVPC-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]ethanone Chemical compound CC(C)CC1=CC=C(C(C)=O)C=C1 KEAGRYYGYWZVPC-UHFFFAOYSA-N 0.000 description 1
- NZGHJIGCMVGJTF-UHFFFAOYSA-N 1-cyclohexyl-4-prop-1-en-2-ylbenzene Chemical compound C1=CC(C(=C)C)=CC=C1C1CCCCC1 NZGHJIGCMVGJTF-UHFFFAOYSA-N 0.000 description 1
- HGBWLVJRAMGLJW-UHFFFAOYSA-N 1-ethenyl-2-methyl-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C=C)C(C)=C1 HGBWLVJRAMGLJW-UHFFFAOYSA-N 0.000 description 1
- PAMLTMDKARKMOU-UHFFFAOYSA-N 2-(3-methoxy-4-phenoxyphenyl)propan-2-ol Chemical compound COC=1C=C(C=CC1OC1=CC=CC=C1)C(C)(C)O PAMLTMDKARKMOU-UHFFFAOYSA-N 0.000 description 1
- JDYOGRRUTFRBDL-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1C1CCCCC1 JDYOGRRUTFRBDL-UHFFFAOYSA-N 0.000 description 1
- YQEYLXLAWZVDQO-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)phenyl]propan-2-ol Chemical compound FC1=CC=C(C=C1)C1=C(C=CC=C1)C(C)(C)O YQEYLXLAWZVDQO-UHFFFAOYSA-N 0.000 description 1
- OHITVHATOPWRRY-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propan-2-ol Chemical compound CC(C)CC1=CC=C(C(C)(C)O)C=C1 OHITVHATOPWRRY-UHFFFAOYSA-N 0.000 description 1
- SFJJGLUATPUIGV-UHFFFAOYSA-N 2-methoxy-1-phenoxy-4-prop-1-en-2-ylbenzene Chemical compound COC1=C(OC2=CC=CC=C2)C=CC(=C1)C(C)=C SFJJGLUATPUIGV-UHFFFAOYSA-N 0.000 description 1
- OSJLDCQZKGVESM-UHFFFAOYSA-N 2-methyl-1-phenoxy-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC(C)=C(OC2=CC=CC=C2)C=C1 OSJLDCQZKGVESM-UHFFFAOYSA-N 0.000 description 1
- OJQGOGRZNQQPHZ-UHFFFAOYSA-N 4-butyl-1-ethenyl-2-methylbenzene Chemical compound CCCCC1=CC=C(C=C)C(C)=C1 OJQGOGRZNQQPHZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9155970A | 1970-11-20 | 1970-11-20 | |
| US12923771A | 1971-03-29 | 1971-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL86932B1 true PL86932B1 (enExample) | 1976-06-30 |
Family
ID=26784083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17353571A PL86932B1 (enExample) | 1970-11-20 | 1971-06-28 |
Country Status (6)
| Country | Link |
|---|---|
| AR (1) | AR205325A1 (enExample) |
| AT (1) | ATA98074A (enExample) |
| ES (3) | ES392719A1 (enExample) |
| NO (1) | NO132724C (enExample) |
| PL (1) | PL86932B1 (enExample) |
| RO (2) | RO68010A (enExample) |
-
1971
- 1971-06-25 NO NO243371A patent/NO132724C/no unknown
- 1971-06-25 AT AT9807471A patent/ATA98074A/de not_active IP Right Cessation
- 1971-06-28 RO RO7184263A patent/RO68010A/ro unknown
- 1971-06-28 ES ES392719A patent/ES392719A1/es not_active Expired
- 1971-06-28 PL PL17353571A patent/PL86932B1/pl unknown
- 1971-06-28 RO RO6748571A patent/RO63814A/ro unknown
-
1972
- 1972-01-01 AR AR24425972A patent/AR205325A1/es active
-
1974
- 1974-01-16 ES ES422352A patent/ES422352A1/es not_active Expired
- 1974-01-16 ES ES422351A patent/ES422351A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA98074A (de) | 1975-06-15 |
| AR205325A1 (es) | 1976-04-30 |
| NO132724C (enExample) | 1975-12-22 |
| ES392719A1 (es) | 1974-12-01 |
| RO68010A (ro) | 1980-12-30 |
| ES422351A1 (es) | 1976-07-16 |
| ES422352A1 (es) | 1976-10-01 |
| RO63814A (fr) | 1979-01-15 |
| NO132724B (enExample) | 1975-09-15 |
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