HU181948B - Process for the resolution of dl-cys- and dl-trans-2,2-dimethyl-3-/2'-methyl-1'-propylene/-cyclopropane-1-carboxylic acid /chrysanthemic acid/ - Google Patents
Process for the resolution of dl-cys- and dl-trans-2,2-dimethyl-3-/2'-methyl-1'-propylene/-cyclopropane-1-carboxylic acid /chrysanthemic acid/ Download PDFInfo
- Publication number
- HU181948B HU181948B HU79RO1050A HURO001050A HU181948B HU 181948 B HU181948 B HU 181948B HU 79RO1050 A HU79RO1050 A HU 79RO1050A HU RO001050 A HURO001050 A HU RO001050A HU 181948 B HU181948 B HU 181948B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- cis
- cyclopropane
- dimethyl
- propylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 title description 15
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 title description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 38
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 229960002221 methylephedrine Drugs 0.000 claims description 8
- FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229940073569 n-methylephedrine Drugs 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- FMCGSUUBYTWNDP-UHFFFAOYSA-N N-Methylephedrine Natural products CN(C)C(C)C(O)C1=CC=CC=C1 FMCGSUUBYTWNDP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 17
- XLOPRKKSAJMMEW-JGVFFNPUSA-N (-)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@H]1[C@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-JGVFFNPUSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- FMCGSUUBYTWNDP-MWLCHTKSSA-N (1s,2r)-2-(dimethylamino)-1-phenylpropan-1-ol Chemical compound CN(C)[C@H](C)[C@@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-MWLCHTKSSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7834591A FR2443452A1 (fr) | 1978-12-08 | 1978-12-08 | Nouveau procede de dedoublement de l'acide dl cis et dl trans chrysanthemique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU181948B true HU181948B (en) | 1983-11-28 |
Family
ID=9215840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79RO1050A HU181948B (en) | 1978-12-08 | 1979-12-06 | Process for the resolution of dl-cys- and dl-trans-2,2-dimethyl-3-/2'-methyl-1'-propylene/-cyclopropane-1-carboxylic acid /chrysanthemic acid/ |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4257976A (en, 2012) |
| JP (1) | JPS56108736A (en, 2012) |
| BE (1) | BE880490A (en, 2012) |
| CA (1) | CA1127180A (en, 2012) |
| CH (1) | CH641751A5 (en, 2012) |
| DE (1) | DE2949384A1 (en, 2012) |
| ES (1) | ES486670A1 (en, 2012) |
| FR (1) | FR2443452A1 (en, 2012) |
| HU (1) | HU181948B (en, 2012) |
| IT (1) | IT1164774B (en, 2012) |
| NL (1) | NL7908881A (en, 2012) |
| SE (1) | SE430984B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU543276B2 (en) * | 1981-06-18 | 1985-04-18 | Stauffer Chemical Company | Resolution of dl-trans-chrysanthemic acid |
| US4542235A (en) * | 1982-04-12 | 1985-09-17 | Sumitomo Chemical Company, Limited | Method for producing an optically active 2,2-dimethylcyclopropanecarboxylic acid |
| US4663474A (en) * | 1983-02-22 | 1987-05-05 | Pfizer Inc. | Synthetic intermediates for a chiral 3-(substituted-phenyl)-4-(3-hydroxypropyl) cyclohexanol |
| WO1993025667A1 (en) * | 1992-06-05 | 1993-12-23 | The Scripps Research Institute | D-enzyme compositions and methods of their use |
| US5447897A (en) * | 1993-05-17 | 1995-09-05 | Shell Oil Company | Ethylene oxide catalyst and process |
| ITMI20050231A1 (it) * | 2005-02-17 | 2006-08-18 | Endura Spa | Processo per l'ottenimento di enantiomeri dell'acido crisantemico |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR92748E (fr) * | 1966-01-26 | 1968-12-20 | Roussel Uclaf | Nouveaux composés optiquement actifs et procédé pour leur utilisation au dédoublement de produits racémiques. |
| FR1536458A (fr) * | 1967-07-07 | 1968-08-16 | Roussel Uclaf | Procédé d'obtention de l'acide d-trans chrysanthémique |
| CH486411A (de) * | 1966-04-27 | 1970-02-28 | Sumitomo Chemical Co | Verfahren zur Herstellung von optisch hochreinem (+)-trans-Chrysanthemummonocarbonsäure-Chininsalz |
| FR1507192A (fr) * | 1966-08-26 | 1967-12-29 | Roussel Uclaf | Nouvelles aryl allylsulfones et procédé de préparation |
| US3739019A (en) * | 1969-07-02 | 1973-06-12 | Sumitomo Chemical Co | Preparation of optically active trans chrysanthemic acid |
| BE755498A (fr) * | 1969-09-12 | 1971-02-01 | Sumitomo Chemical Co | Preparation d'acide chrysanthemique optiquement |
| HU165117B (en, 2012) * | 1971-08-12 | 1974-06-28 | ||
| BE790240A (fr) * | 1971-10-19 | 1973-02-15 | Sumitomo Chemical Co | Procede de preparation de l'acide mixte (+)-cis, (+)-trans- chrysanthemique |
| JPS5123497B2 (en, 2012) * | 1972-01-07 | 1976-07-17 | ||
| JPS4992049A (en, 2012) * | 1973-01-09 | 1974-09-03 | ||
| JPS51143647A (en) * | 1975-06-06 | 1976-12-10 | Sumitomo Chem Co Ltd | Process for obtaining optically active trans-2,2-dimethyl-3-(2,2-dichl orovinyl) cyclopropanecarboxylic acid |
-
1978
- 1978-12-08 FR FR7834591A patent/FR2443452A1/fr active Granted
-
1979
- 1979-10-23 SE SE7908765A patent/SE430984B/sv not_active IP Right Cessation
- 1979-11-20 US US06/096,028 patent/US4257976A/en not_active Expired - Lifetime
- 1979-12-06 CA CA341,406A patent/CA1127180A/fr not_active Expired
- 1979-12-06 HU HU79RO1050A patent/HU181948B/hu not_active IP Right Cessation
- 1979-12-07 DE DE19792949384 patent/DE2949384A1/de active Granted
- 1979-12-07 ES ES486670A patent/ES486670A1/es not_active Expired
- 1979-12-07 CH CH1087779A patent/CH641751A5/fr not_active IP Right Cessation
- 1979-12-07 BE BE0/198472A patent/BE880490A/fr not_active IP Right Cessation
- 1979-12-07 IT IT51027/79A patent/IT1164774B/it active
- 1979-12-07 JP JP15822679A patent/JPS56108736A/ja active Granted
- 1979-12-10 NL NL7908881A patent/NL7908881A/nl active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| DE2949384A1 (de) | 1980-06-26 |
| ES486670A1 (es) | 1980-05-16 |
| DE2949384C2 (en, 2012) | 1990-09-13 |
| US4257976A (en) | 1981-03-24 |
| IT1164774B (it) | 1987-04-15 |
| SE430984B (sv) | 1983-12-27 |
| SE7908765L (sv) | 1980-06-09 |
| FR2443452B1 (en, 2012) | 1981-08-14 |
| CA1127180A (fr) | 1982-07-06 |
| JPS56108736A (en) | 1981-08-28 |
| JPS6410508B2 (en, 2012) | 1989-02-22 |
| IT7951027A0 (it) | 1979-12-07 |
| NL7908881A (nl) | 1980-06-10 |
| BE880490A (fr) | 1980-06-09 |
| CH641751A5 (fr) | 1984-03-15 |
| FR2443452A1 (fr) | 1980-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |