BE572479A - - Google Patents
Info
- Publication number
- BE572479A BE572479A BE572479DA BE572479A BE 572479 A BE572479 A BE 572479A BE 572479D A BE572479D A BE 572479DA BE 572479 A BE572479 A BE 572479A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- compound
- general formula
- treatment
- dichloroacetylation
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 135
- 238000000034 method Methods 0.000 claims description 25
- 238000006460 hydrolysis reaction Methods 0.000 claims description 22
- -1 dichloroacetyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- UFVLRHXFRXZBHS-UHFFFAOYSA-N 3,3,3-trichloro-2-hydroxypropanenitrile Chemical compound N#CC(O)C(Cl)(Cl)Cl UFVLRHXFRXZBHS-UHFFFAOYSA-N 0.000 claims description 5
- 101700040785 CHR5 Proteins 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000001184 potassium carbonate Substances 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N 3,4-dihydro-2H-pyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 3
- RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 claims description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N Dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 2
- STZZWJCGRKXEFF-UHFFFAOYSA-N Dichloroacetonitrile Chemical compound ClC(Cl)C#N STZZWJCGRKXEFF-UHFFFAOYSA-N 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 101700041618 nhr-4 Proteins 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims 3
- 239000002262 Schiff base Substances 0.000 claims 1
- 150000004753 Schiff bases Chemical class 0.000 claims 1
- 238000006640 acetylation reaction Methods 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000002844 melting Methods 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 12
- 230000011987 methylation Effects 0.000 description 11
- 238000007069 methylation reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WIWSJWAXUVHJBW-UHFFFAOYSA-N 2,2-dichloro-N-(4-hydroxyphenyl)acetamide Chemical compound OC1=CC=C(NC(=O)C(Cl)Cl)C=C1 WIWSJWAXUVHJBW-UHFFFAOYSA-N 0.000 description 8
- 238000004364 calculation method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WYODKEXCSBRCDL-UHFFFAOYSA-N [4-(methylamino)phenyl] benzoate Chemical compound C1=CC(NC)=CC=C1OC(=O)C1=CC=CC=C1 WYODKEXCSBRCDL-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- BRWPSNHSOBHFQP-UHFFFAOYSA-N [4-(methylamino)phenyl] acetate Chemical compound CNC1=CC=C(OC(C)=O)C=C1 BRWPSNHSOBHFQP-UHFFFAOYSA-N 0.000 description 4
- LOCNFWNVXOMBSH-UHFFFAOYSA-N [4-[(2,2-dichloroacetyl)amino]phenyl] acetate Chemical compound CC(=O)OC1=CC=C(NC(=O)C(Cl)Cl)C=C1 LOCNFWNVXOMBSH-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- BVTLIIQDQAUXOI-UHFFFAOYSA-N 4-(benzylideneamino)phenol Chemical compound C1=CC(O)=CC=C1N=CC1=CC=CC=C1 BVTLIIQDQAUXOI-UHFFFAOYSA-N 0.000 description 3
- MOXTXYMFGOOPHY-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OC1=CC=C(C=C1)NC(C(Cl)Cl)=O Chemical compound C(C1=CC=CC=C1)(=O)OC1=CC=C(C=C1)NC(C(Cl)Cl)=O MOXTXYMFGOOPHY-UHFFFAOYSA-N 0.000 description 3
- 229940087562 Sodium Acetate Trihydrate Drugs 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- AYRVGWHSXIMRAB-UHFFFAOYSA-M sodium acetate trihydrate Chemical compound O.O.O.[Na+].CC([O-])=O AYRVGWHSXIMRAB-UHFFFAOYSA-M 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- IFIWFBLNBUMQKX-UHFFFAOYSA-N (4-formamidophenyl) benzoate Chemical compound C1=CC(NC=O)=CC=C1OC(=O)C1=CC=CC=C1 IFIWFBLNBUMQKX-UHFFFAOYSA-N 0.000 description 2
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- LHMWHZXZMMLYKI-UHFFFAOYSA-N N-(4-hydroxyphenyl)formamide Chemical compound OC1=CC=C(NC=O)C=C1 LHMWHZXZMMLYKI-UHFFFAOYSA-N 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N Potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000003569 amebicidal Effects 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229940095076 benzaldehyde Drugs 0.000 description 2
- 238000006480 benzoylation reaction Methods 0.000 description 2
- WMJRPJZQQSSDBU-UHFFFAOYSA-L disodium;sulfite;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])=O WMJRPJZQQSSDBU-UHFFFAOYSA-L 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KJSVAEGLTPBKAA-UHFFFAOYSA-N 2,2-dichloro-N-phenylacetamide Chemical compound ClC(Cl)C(=O)NC1=CC=CC=C1 KJSVAEGLTPBKAA-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- OHYPPUOVSUINHM-UHFFFAOYSA-N 4-(methylamino)phenol;sulfuric acid Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1 OHYPPUOVSUINHM-UHFFFAOYSA-N 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229960002327 Chloral Hydrate Drugs 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N Chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N Sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000000994 depressed Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating Effects 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004430 oxygen atoms Chemical group O* 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE572479A true BE572479A (xx) |
Family
ID=190269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE572479D BE572479A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE572479A (xx) |
-
0
- BE BE572479D patent/BE572479A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2658513A1 (fr) | Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r). | |
| BE572479A (xx) | ||
| EP0184572B1 (fr) | Procédé de préparation d'acides alpha-hydroxy-alcanoiques | |
| FR2467842A1 (fr) | Procede pour la production d'iminodiacetonitrile | |
| EP0221815B1 (fr) | Procédé pour la fabrication d'acides alkanoiques | |
| BE500594A (xx) | ||
| EP0124407B1 (fr) | Procédé de préparation d'acides alkanoiques | |
| BE503348A (xx) | ||
| BE512433A (xx) | ||
| FR2572397A1 (fr) | Procede de preparation de l'acide 3-hydroxy-3-methyl-glutarique | |
| BE482075A (xx) | ||
| BE876979A (fr) | Procede de preparation d'ester de phtalidyle de l'acide penicillanique | |
| EP0627403A1 (fr) | Procédé de préparation d'acides hydroxyphénylacétiques | |
| CH426858A (fr) | Procédé de préparation de nouveaux dérivés colchiciques | |
| BE516840A (xx) | ||
| BE507032A (xx) | ||
| BE482321A (xx) | ||
| CH378903A (fr) | Procédé de préparation d'un dérivé de la dichloracétanilide | |
| CH315886A (fr) | Procédé de préparation d'une N-dichloracétamide hétérocyclique | |
| BE738214A (en) | 2,2-Di-methyl-omega-aryloxyalkane acids, salts and esters | |
| BE442126A (xx) | ||
| CH298327A (fr) | Procédé de préparation d'une forme thérapeutiquement active de la thréo-2-dichlorométhyl-4-hydroxyméthyl-5-p-nitrophényl-oxazoline-2. | |
| BE503876A (xx) | ||
| BE517755A (xx) | ||
| BE505572A (xx) |