NO129521B - - Google Patents
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- Publication number
- NO129521B NO129521B NO418869A NO418869A NO129521B NO 129521 B NO129521 B NO 129521B NO 418869 A NO418869 A NO 418869A NO 418869 A NO418869 A NO 418869A NO 129521 B NO129521 B NO 129521B
- Authority
- NO
- Norway
- Prior art keywords
- water
- general formula
- mixture
- solution
- biphenylyl
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- -1 4-(p-biphenylyl)-3-hydroxybutyric acid nitrile Chemical class 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- SFHXNWGGDWFBBR-UHFFFAOYSA-N 1-chloro-3-(4-phenylphenyl)propan-2-ol Chemical compound C1=CC(CC(CCl)O)=CC=C1C1=CC=CC=C1 SFHXNWGGDWFBBR-UHFFFAOYSA-N 0.000 claims 1
- MNZZDFVDWXMEPF-UHFFFAOYSA-N 3-hydroxy-4-(2-phenylphenyl)butanamide Chemical compound C1(=C(C=CC=C1)CC(CC(=O)N)O)C1=CC=CC=C1 MNZZDFVDWXMEPF-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MEYAGVCRWQSMPR-UHFFFAOYSA-N 3-hydroxy-4-phenylbutanamide Chemical compound OC(CC(=O)N)CC1=CC=CC=C1 MEYAGVCRWQSMPR-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- TVDCSPSRGSLXOV-UHFFFAOYSA-N 1-bromo-3-chloropropan-2-ol Chemical compound ClCC(O)CBr TVDCSPSRGSLXOV-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- VBZRCYGKCAOPJW-UHFFFAOYSA-N 1-chloro-3-phenylpropan-2-ol Chemical compound ClCC(O)CC1=CC=CC=C1 VBZRCYGKCAOPJW-UHFFFAOYSA-N 0.000 description 1
- BAUSLKUKOKYZAH-UHFFFAOYSA-N C(CCC)OC1=CC=C(C=C1)CC(CC(=O)N)O Chemical compound C(CCC)OC1=CC=C(C=C1)CC(CC(=O)N)O BAUSLKUKOKYZAH-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100134025 Rattus norvegicus Lat2 gene Proteins 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
- PTGSEPPUEHTQIX-UHFFFAOYSA-M [Br-].CCCCOC1=CC=C([Mg+])C=C1 Chemical compound [Br-].CCCCOC1=CC=C([Mg+])C=C1 PTGSEPPUEHTQIX-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO418869A NO129521B (enrdf_load_stackoverflow) | 1964-07-23 | 1969-10-22 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29654/64A GB1040735A (en) | 1964-07-23 | 1964-07-23 | 4-aryl-3-hydroxybutyric acid and esters, amides and salts thereof |
| NO159060A NO122066B (enrdf_load_stackoverflow) | 1964-07-23 | 1965-07-22 | |
| NO418869A NO129521B (enrdf_load_stackoverflow) | 1964-07-23 | 1969-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129521B true NO129521B (enrdf_load_stackoverflow) | 1974-04-22 |
Family
ID=27258831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO418869A NO129521B (enrdf_load_stackoverflow) | 1964-07-23 | 1969-10-22 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO129521B (enrdf_load_stackoverflow) |
-
1969
- 1969-10-22 NO NO418869A patent/NO129521B/no unknown
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