DE3024265C2 - - Google Patents
Info
- Publication number
- DE3024265C2 DE3024265C2 DE3024265A DE3024265A DE3024265C2 DE 3024265 C2 DE3024265 C2 DE 3024265C2 DE 3024265 A DE3024265 A DE 3024265A DE 3024265 A DE3024265 A DE 3024265A DE 3024265 C2 DE3024265 C2 DE 3024265C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- carbon atoms
- acid
- optically active
- alkali
- 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
- 239000002253 acid Substances 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 claims description 26
- 150000001447 alkali salts Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 21
- -1 alkali metal salt Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000003513 alkali Substances 0.000 claims description 18
- CTDIKDIZNAGMFK-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxycarbonyl]thiomorpholine-3-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCSCC1C(O)=O CTDIKDIZNAGMFK-UHFFFAOYSA-N 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 238000011065 in-situ storage Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940031826 phenolate Drugs 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229950011008 tetrachloroethylene Drugs 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 4
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- KTAVXDDWEGVLRN-UHFFFAOYSA-N 2-naphthalen-1-yloxypropanoic acid Chemical compound C1=CC=C2C(OC(C)C(O)=O)=CC=CC2=C1 KTAVXDDWEGVLRN-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- SXERGJJQSKIUIC-SSDOTTSWSA-N (2r)-2-phenoxypropanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC=C1 SXERGJJQSKIUIC-SSDOTTSWSA-N 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 2
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZLSWBLPERHFHIS-UHFFFAOYSA-N Fenoprop Chemical compound OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000002152 aqueous-organic solution Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- YIGXGYDKDDWZLS-UHFFFAOYSA-N 2-(2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1C YIGXGYDKDDWZLS-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- DPRSKCAGYLXDCY-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1Cl DPRSKCAGYLXDCY-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005506 Diclofop Substances 0.000 description 1
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 description 1
- 239000005585 Napropamide Substances 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7917423A FR2460286A1 (fr) | 1979-06-29 | 1979-06-29 | Procede de preparation d'acide phenoxy-2 propioniques optiquement actifs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3024265A1 DE3024265A1 (de) | 1981-01-15 |
| DE3024265C2 true DE3024265C2 (en, 2012) | 1990-04-19 |
Family
ID=9227531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803024265 Granted DE3024265A1 (de) | 1979-06-29 | 1980-06-27 | Verfahren zur herstellung von optisch aktiven aryloxylalkansaeure-verbindungen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4766220A (en, 2012) |
| JP (1) | JPS568344A (en, 2012) |
| AT (1) | AT370079B (en, 2012) |
| BE (1) | BE884078A (en, 2012) |
| BR (1) | BR8004037A (en, 2012) |
| CA (1) | CA1131249A (en, 2012) |
| CH (2) | CH660878A5 (en, 2012) |
| DE (1) | DE3024265A1 (en, 2012) |
| DK (1) | DK159144C (en, 2012) |
| ES (1) | ES492844A0 (en, 2012) |
| FR (1) | FR2460286A1 (en, 2012) |
| IE (1) | IE49949B1 (en, 2012) |
| IT (1) | IT1131823B (en, 2012) |
| LU (1) | LU82562A1 (en, 2012) |
| NL (1) | NL8003363A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3240805A1 (de) * | 1982-11-05 | 1984-05-10 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von hydroxy-phenoxy-alkancarbonsaeuren |
| US4831147A (en) * | 1988-07-05 | 1989-05-16 | The Dow Chemical Company | Resolution of enantiomers of herbicidal 2-(4-aryloxyphenoxy) propionates by chiral two-phase extraction |
| FR2719042B1 (fr) * | 1994-04-25 | 1996-05-15 | Rhone Poulenc Chimie | Procédé de préparation d'un acide alpha-(hydroxyphénoxy)- alcanecarboxylique optiquement actif. |
| DE4446387A1 (de) * | 1994-12-23 | 1996-06-27 | Basf Ag | Verfahren zur Herstellung fester, freifließender wasserlöslicher Salze von Aryloxi-C¶1¶-C¶4¶-alkancarbonsäuren |
| US6184415B1 (en) | 1999-11-01 | 2001-02-06 | Albemarle Corporation | Production of chiral non-racemic 2-halopropionic acid or salt thereof |
| JP2010526059A (ja) * | 2007-05-04 | 2010-07-29 | ユナイテッド フォスフォラス リミテッド | 高純度Ｄ−（−）−Ｎ，Ｎ−ジエチル−２−（α−ナフトキシ）プロピオンアミドの製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE586247A (en, 2012) * | 1959-01-07 | |||
| US3378582A (en) * | 1964-03-20 | 1968-04-16 | Merck & Co Inc | (alpha-phenoxy)-and (alpha-phenylthio)-omegaphenyl-alkanoic acids |
| US3454626A (en) * | 1965-01-21 | 1969-07-08 | Bristol Myers Co | Racemic monocarboxylic acid resolution using dehydroabietylamine |
| FR1479271A (fr) * | 1965-12-17 | 1967-05-05 | Rhone Poulenc Sa | Nouveau procédé de préparation d'acides phénoxy-2 propioniques optiquement actifs |
| US4173709A (en) * | 1965-12-17 | 1979-11-06 | Rhone-Poulenc S.A. | Process for the preparation of dextrorotatory 2-phenoxypropionic acid derivatives |
| US3707549A (en) * | 1967-12-05 | 1972-12-26 | Lilly Co Eli | Alpha-substituted hydrocinnamic acids and derivatives thereof |
| GB1499508A (en) * | 1974-12-06 | 1978-02-01 | Ici Ltd | 3,3,3-trifluoropropionic acid derivatives |
| CA1147348A (en) * | 1978-09-19 | 1983-05-31 | Willem Eveleens | Process for the preparation of optically active 2-phenoxy propionic acids and herbicidal preparations containing such acids |
| DE2949681A1 (de) * | 1979-12-11 | 1981-07-02 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von optisch aktiven d-(phenoxy, bzw. benzyl)-phenoxypropionsaeuren und ihren alkalisalzen |
| DE2949728A1 (de) * | 1979-12-11 | 1981-06-19 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von optisch aktiven 2-phenoxypropionsaeuren |
-
1979
- 1979-06-29 FR FR7917423A patent/FR2460286A1/fr active Granted
-
1980
- 1980-06-09 NL NL8003363A patent/NL8003363A/nl not_active Application Discontinuation
- 1980-06-12 IT IT22735/80A patent/IT1131823B/it active
- 1980-06-19 CH CH4830/85A patent/CH660878A5/fr not_active IP Right Cessation
- 1980-06-19 CH CH4727/80A patent/CH653981A5/fr not_active IP Right Cessation
- 1980-06-27 ES ES492844A patent/ES492844A0/es active Granted
- 1980-06-27 JP JP8770980A patent/JPS568344A/ja active Granted
- 1980-06-27 DE DE19803024265 patent/DE3024265A1/de active Granted
- 1980-06-27 IE IE1339/80A patent/IE49949B1/en not_active IP Right Cessation
- 1980-06-27 CA CA355,025A patent/CA1131249A/en not_active Expired
- 1980-06-27 AT AT0339480A patent/AT370079B/de not_active IP Right Cessation
- 1980-06-27 LU LU82562A patent/LU82562A1/fr unknown
- 1980-06-27 BE BE0/201235A patent/BE884078A/fr not_active IP Right Cessation
- 1980-06-27 DK DK278580A patent/DK159144C/da not_active IP Right Cessation
- 1980-06-27 BR BR8004037A patent/BR8004037A/pt unknown
-
1985
- 1985-07-30 US US06/761,302 patent/US4766220A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IT1131823B (it) | 1986-06-25 |
| DK278580A (da) | 1980-12-30 |
| FR2460286B1 (en, 2012) | 1983-11-25 |
| NL8003363A (nl) | 1980-12-31 |
| ES8203817A1 (es) | 1981-11-01 |
| DE3024265A1 (de) | 1981-01-15 |
| JPS568344A (en) | 1981-01-28 |
| IE49949B1 (en) | 1986-01-22 |
| CA1131249A (en) | 1982-09-07 |
| CH660878A5 (fr) | 1987-05-29 |
| BR8004037A (pt) | 1981-01-21 |
| DK159144C (da) | 1991-02-18 |
| ES492844A0 (es) | 1981-11-01 |
| DK159144B (da) | 1990-09-10 |
| JPS6410506B2 (en, 2012) | 1989-02-22 |
| CH653981A5 (fr) | 1986-01-31 |
| FR2460286A1 (fr) | 1981-01-23 |
| ATA339480A (de) | 1982-07-15 |
| AT370079B (de) | 1983-02-25 |
| IE801339L (en) | 1980-12-29 |
| LU82562A1 (fr) | 1982-01-20 |
| US4766220A (en) | 1988-08-23 |
| IT8022735A0 (it) | 1980-06-12 |
| BE884078A (fr) | 1980-12-29 |
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