JPH0324468B2 - - Google Patents
Info
- Publication number
- JPH0324468B2 JPH0324468B2 JP61306716A JP30671686A JPH0324468B2 JP H0324468 B2 JPH0324468 B2 JP H0324468B2 JP 61306716 A JP61306716 A JP 61306716A JP 30671686 A JP30671686 A JP 30671686A JP H0324468 B2 JPH0324468 B2 JP H0324468B2
- Authority
- JP
- Japan
- Prior art keywords
- phenoxy
- phenyl
- solution
- compound
- alcohol
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- DKGMALJGFUHPGB-UHFFFAOYSA-N 2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CCC1=CC=CC(OC=2C=CC=CC=2)=C1 DKGMALJGFUHPGB-UHFFFAOYSA-N 0.000 claims description 9
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 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 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 6
- AVCXUPSTLHKNGB-UHFFFAOYSA-N 2-cyano-2-(3-phenoxyphenyl)acetic acid Chemical compound OC(=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 AVCXUPSTLHKNGB-UHFFFAOYSA-N 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 230000001035 methylating effect Effects 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000003756 stirring Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- RDJGLLICXDHJDY-UHFFFAOYSA-N fenoprofen Chemical compound OC(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- SPRFQFFNDBIQDY-UHFFFAOYSA-N 2-cyano-2-(3-phenoxyphenyl)propanamide Chemical compound N#CC(C)(C(N)=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 SPRFQFFNDBIQDY-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- -1 alkyl phenoxy-phenyl-acetic acid Chemical compound 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- RFALKMQNBPHELA-UHFFFAOYSA-N ethyl 2-cyano-2-(3-phenoxyphenyl)propanoate Chemical compound CCOC(=O)C(C)(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 RFALKMQNBPHELA-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012022 methylating agents Substances 0.000 description 3
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 2
- QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 2
- LEMRHTTWKDVQEI-UHFFFAOYSA-N 2-(3-phenoxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 LEMRHTTWKDVQEI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MIHRVXYXORIINI-UHFFFAOYSA-N ethyl 2-cyanopropionate Chemical compound CCOC(=O)C(C)C#N MIHRVXYXORIINI-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- XUDXNGUORATCNY-UHFFFAOYSA-N methyl 2-cyano-2-(3-phenoxyphenyl)propanoate Chemical compound COC(=O)C(C)(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XUDXNGUORATCNY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
- NAFPHJPIASZFMX-UHFFFAOYSA-N 1-(1-bromoethyl)-3-phenoxybenzene Chemical compound CC(Br)C1=CC=CC(OC=2C=CC=CC=2)=C1 NAFPHJPIASZFMX-UHFFFAOYSA-N 0.000 description 1
- INZVQPCHWIUUFV-UHFFFAOYSA-N 1-(2-methylpropyl)-3-phenoxybenzene Chemical compound CC(C)CC1=CC=CC(OC=2C=CC=CC=2)=C1 INZVQPCHWIUUFV-UHFFFAOYSA-N 0.000 description 1
- MYWBBBSIAHHXJK-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanol Chemical compound CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 MYWBBBSIAHHXJK-UHFFFAOYSA-N 0.000 description 1
- FZCDBGYCFVKRDV-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDBGYCFVKRDV-UHFFFAOYSA-N 0.000 description 1
- OBTDVRGUJLGMIN-UHFFFAOYSA-N 1-phenoxy-3-prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC(OC=2C=CC=CC=2)=C1 OBTDVRGUJLGMIN-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- FPJBPTQTHPZNBE-UHFFFAOYSA-N 2-cyano-2-(3-phenoxyphenyl)propanoic acid Chemical compound N#CC(C)(C(O)=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FPJBPTQTHPZNBE-UHFFFAOYSA-N 0.000 description 1
- DASYJICSSLWYAG-UHFFFAOYSA-N 2-cyanopropanamide Chemical compound N#CC(C)C(N)=O DASYJICSSLWYAG-UHFFFAOYSA-N 0.000 description 1
- XFKRMUHUTOKOBT-UHFFFAOYSA-N 2-methyl-2-(3-phenoxyphenyl)propanedioic acid Chemical compound OC(=O)C(C)(C(O)=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 XFKRMUHUTOKOBT-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- LKPVHTAWGPBJMM-UHFFFAOYSA-M [O-]C1=CC=CC=C1.[Mg+]C1=CC=CC=C1 Chemical compound [O-]C1=CC=CC=C1.[Mg+]C1=CC=CC=C1 LKPVHTAWGPBJMM-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- FGYDHYCFHBSNPE-UHFFFAOYSA-N diethyl phenylmalonate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1 FGYDHYCFHBSNPE-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- VGLCBSOALKYKJU-UHFFFAOYSA-N ethyl 2-cyano-2-(3-phenoxyphenyl)acetate Chemical compound CCOC(=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 VGLCBSOALKYKJU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229960001419 fenoprofen Drugs 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- CUGDBFARXMYFIW-UHFFFAOYSA-N methyl 2-cyano-2-(3-phenoxyphenyl)acetate Chemical compound COC(=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 CUGDBFARXMYFIW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- FYWSTUCDSVYLPV-UHFFFAOYSA-N nitrooxythallium Chemical compound [Tl+].[O-][N+]([O-])=O FYWSTUCDSVYLPV-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001894 | 1978-12-29 | ||
| HU2251/CI-1894/1978 | 1978-12-29 | ||
| HU2251/CI-1979/1979 | 1979-10-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62167750A JPS62167750A (ja) | 1987-07-24 |
| JPH0324468B2 true JPH0324468B2 (fr) | 1991-04-03 |
Family
ID=10994734
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16842879A Granted JPS55113755A (en) | 1978-12-29 | 1979-12-26 | Manufacture of 22*33phenoxyyphenyl**propionic acid |
| JP30671686A Granted JPS62167750A (ja) | 1978-12-29 | 1986-12-24 | ２―シアノ―２―（３―フェノキシ―フェニル）―プロピオン酸アミドおよびその製法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16842879A Granted JPS55113755A (en) | 1978-12-29 | 1979-12-26 | Manufacture of 22*33phenoxyyphenyl**propionic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JPS55113755A (fr) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50151838A (fr) * | 1974-05-16 | 1975-12-06 | ||
| JPS5145586A (fr) * | 1974-10-16 | 1976-04-19 | Hitachi Ltd |
-
1979
- 1979-12-26 JP JP16842879A patent/JPS55113755A/ja active Granted
-
1986
- 1986-12-24 JP JP30671686A patent/JPS62167750A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50151838A (fr) * | 1974-05-16 | 1975-12-06 | ||
| JPS5145586A (fr) * | 1974-10-16 | 1976-04-19 | Hitachi Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62167750A (ja) | 1987-07-24 |
| JPH0440337B2 (fr) | 1992-07-02 |
| JPS55113755A (en) | 1980-09-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0368026B2 (fr) | ||
| JPS6222740A (ja) | ｐ−ヒドロキシベンズアルデヒドの単離法 | |
| US4393008A (en) | 2-Cyano-2-(3-phenoxy-phenyl)-propionic acid amide and preparation thereof | |
| JPH0324468B2 (fr) | ||
| JPS584699B2 (ja) | 置換フエニル酢酸誘導体及びその製法 | |
| JPH02223542A (ja) | ヒドロアトロパ酸誘導体およびそのエステルの製造方法 | |
| US4022814A (en) | Iodine containing organic carbonates for use as radiographic agents | |
| BE1007058A3 (fr) | Un procede nouveau pour la preparation de l'acide 5-(2,5-dimethylphenoxy)-2,2-dimethyl pentanoique. | |
| JPS584698B2 (ja) | ２−（３−ベンゾイルフエニル）プロピオン酸の製造方法 | |
| JP3869531B2 (ja) | ビフェニル誘導体の製造法 | |
| CA2204201A1 (fr) | Methode pour preparer l'acide 4,5-dichloro-2-methylbenzoique | |
| SU793379A3 (ru) | Способ получени производных -нафтилпропионовой кислоты | |
| BE858864A (fr) | Nouveaux esters d'acides phenyl- et pyridine-3-carboxylique et procede permettant leur preparation | |
| JPH03130252A (ja) | ２―アミノ―５―メチルベンゾフェノン類及びその製造法 | |
| US3206473A (en) | Sulfolanylalkanoic acids and esters thereof | |
| JPS581097B2 (ja) | 光学活性α−置換アリ−ル酢酸のラセミ化方法 | |
| JPH0665245A (ja) | ピリジン−２，３−ジカルボン酸無水物の製造法 | |
| JPS61118348A (ja) | ヒドロキシメチレンアルコキシ酢酸エステルの製造方法 | |
| SU545250A3 (ru) | Способ получени замещенной бифенилилмасл ной кислоты или ее сложных эфиров или ее солей | |
| KR860000848B1 (ko) | 소염진통 작용을 갖는 아릴알칸산 유도체의 프탈리딜에스테르 제조방법 | |
| Stephen et al. | XXXII.—αδ-Derivatives of adipic and β-methyladipic acids, and the preparation of muconic and β-methylmuconic acids | |
| JPS5821897B2 (ja) | ２− フエニルプロピオンアルデヒドユウドウタイノ セイゾウホウ | |
| JPH0469137B2 (fr) | ||
| JPS5819662B2 (ja) | ２↓−ヒドロキシ↓−３↓−ブテン酸誘導体の製造法 | |
| FR2556341A1 (fr) | Nouveau procede de preparation de l'acide hydroxy-3 methyl-3 glutarique |