SU400077A1 - - Google Patents
Info
- Publication number
- SU400077A1 SU400077A1 SU18621A SU18621A SU400077A1 SU 400077 A1 SU400077 A1 SU 400077A1 SU 18621 A SU18621 A SU 18621A SU 18621 A SU18621 A SU 18621A SU 400077 A1 SU400077 A1 SU 400077A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ethyl ester
- ethyl
- water
- ester
- Prior art date
Links
- 239000002253 acid Substances 0.000 description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 125000004494 ethyl ester group Chemical group 0.000 description 24
- -1 2-iodoethoxy Chemical group 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- PASUDGKNNPSRBK-UHFFFAOYSA-N 2-ethoxy-2-methylbutanoic acid Chemical compound CCOC(C)(CC)C(O)=O PASUDGKNNPSRBK-UHFFFAOYSA-N 0.000 description 4
- MBBZMMPHUWSWHV-BDVNFPICSA-N Meglumine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Chemical group 0.000 description 4
- 239000002184 metal Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- SCNMDYBNRBCFEX-UHFFFAOYSA-N ethyl 2-(2-chloroethoxymethyl)butanoate Chemical compound CCOC(=O)C(CC)COCCCl SCNMDYBNRBCFEX-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 239000001187 sodium carbonate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ZXVHNKWBPXSYHF-UHFFFAOYSA-N 2-butoxy-2-methylbutanoic acid Chemical compound CCCCOC(C)(CC)C(O)=O ZXVHNKWBPXSYHF-UHFFFAOYSA-N 0.000 description 2
- WBWRBVHCMUPBLI-UHFFFAOYSA-N 2-butoxy-2-methylpropanoic acid Chemical compound CCCCOC(C)(C)C(O)=O WBWRBVHCMUPBLI-UHFFFAOYSA-N 0.000 description 2
- DTHDOSLHTCAQFQ-UHFFFAOYSA-N 2-methyl-2-propoxybutanoic acid Chemical compound CCCOC(C)(CC)C(O)=O DTHDOSLHTCAQFQ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BYGSMQKWFWAJNB-UHFFFAOYSA-N ICCOCC(C(=O)O)CC Chemical compound ICCOCC(C(=O)O)CC BYGSMQKWFWAJNB-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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- LUTWEKBTDWRTSE-UHFFFAOYSA-N 1-chloro-2-(chloromethoxy)ethane Chemical compound ClCCOCCl LUTWEKBTDWRTSE-UHFFFAOYSA-N 0.000 description 1
- SYXHIBUNEXWYEW-UHFFFAOYSA-N 2-(2-chloroethoxy)propanoic acid Chemical compound OC(=O)C(C)OCCCl SYXHIBUNEXWYEW-UHFFFAOYSA-N 0.000 description 1
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 1
- ZCGZOPIPEZCKKQ-UHFFFAOYSA-N 2-ethoxy-2-methylpropanoic acid Chemical compound CCOC(C)(C)C(O)=O ZCGZOPIPEZCKKQ-UHFFFAOYSA-N 0.000 description 1
- SWACCTXALJHTOE-UHFFFAOYSA-N 2-methyl-2-propoxypropanoic acid Chemical compound CCCOC(C)(C)C(O)=O SWACCTXALJHTOE-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- WCWGXOFPXRLOQF-UHFFFAOYSA-N C(C)(=O)NC=1C(=C(OCC(C(=O)O)(C)OCC)C(=CC1I)I)I Chemical compound C(C)(=O)NC=1C(=C(OCC(C(=O)O)(C)OCC)C(=CC1I)I)I WCWGXOFPXRLOQF-UHFFFAOYSA-N 0.000 description 1
- ZNUKTXYOEUEJOK-UHFFFAOYSA-N C(C)(=O)NC=1C(=C(OCC(C(=O)O)(CC)OCCCC)C(=CC1I)I)I Chemical compound C(C)(=O)NC=1C(=C(OCC(C(=O)O)(CC)OCCCC)C(=CC1I)I)I ZNUKTXYOEUEJOK-UHFFFAOYSA-N 0.000 description 1
- CVOZLIBGQAUAIC-UHFFFAOYSA-N C(C)OC(C(COCCCCl)CC)=O Chemical compound C(C)OC(C(COCCCCl)CC)=O CVOZLIBGQAUAIC-UHFFFAOYSA-N 0.000 description 1
- KXZIBANDBFLTTR-UHFFFAOYSA-N C(C)OC(C(COCCI)C)=O Chemical compound C(C)OC(C(COCCI)C)=O KXZIBANDBFLTTR-UHFFFAOYSA-N 0.000 description 1
- UHEPVJLCZBCTFG-UHFFFAOYSA-N C(C)OC(C(COCCI)CC)=O Chemical compound C(C)OC(C(COCCI)CC)=O UHEPVJLCZBCTFG-UHFFFAOYSA-N 0.000 description 1
- BPLPANYMHXJFOX-UHFFFAOYSA-N CC(=O)NC1=C(I)C=C(I)C(O)=C1I Chemical compound CC(=O)NC1=C(I)C=C(I)C(O)=C1I BPLPANYMHXJFOX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HCRBXQFHJMCTLF-UHFFFAOYSA-N Ethyl 2-methylbutyrate Chemical compound CCOC(=O)C(C)CC HCRBXQFHJMCTLF-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
- 229940083599 Sodium Iodide Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- KXEJYAHCKOFCEL-UHFFFAOYSA-N [Na].C(C)(=O)NC=1C(=C(C(=CC1I)I)O)I Chemical compound [Na].C(C)(=O)NC=1C(=C(C(=CC1I)I)O)I KXEJYAHCKOFCEL-UHFFFAOYSA-N 0.000 description 1
- CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000005020 pharmaceutical industry Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU400077A1 true SU400077A1 (ja) |
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