DE2030003A1 - alpha (p Chlor) phenoxy isobutter saure eckige Klammer auf 2 (p Chlor) 'phenoxy 2 methyl eckige Klammer zu propylester und Verfahren zur Herstel lung derselben - Google Patents
alpha (p Chlor) phenoxy isobutter saure eckige Klammer auf 2 (p Chlor) 'phenoxy 2 methyl eckige Klammer zu propylester und Verfahren zur Herstel lung derselbenInfo
- Publication number
- DE2030003A1 DE2030003A1 DE19702030003 DE2030003A DE2030003A1 DE 2030003 A1 DE2030003 A1 DE 2030003A1 DE 19702030003 DE19702030003 DE 19702030003 DE 2030003 A DE2030003 A DE 2030003A DE 2030003 A1 DE2030003 A1 DE 2030003A1
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- phenoxy
- square brackets
- methyl
- acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title claims description 4
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 title 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000000879 anti-atherosclerotic effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702030003 DE2030003A1 (de) | 1970-06-18 | 1970-06-18 | alpha (p Chlor) phenoxy isobutter saure eckige Klammer auf 2 (p Chlor) 'phenoxy 2 methyl eckige Klammer zu propylester und Verfahren zur Herstel lung derselben |
| CH872271A CH557325A (de) | 1970-06-18 | 1971-06-15 | Verfahren zur herstellung von (alpha)-(p-chlor)-phenoxy-isobuttersaeure-(2'-(p-chlor)-phenoxy-2'-methyl)-propylester. |
| GB1291010D GB1291010A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-06-18 | 1971-06-16 | |
| FR7121792A FR2100774B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-06-18 | 1971-06-16 | |
| AT525371A AT308081B (de) | 1970-06-18 | 1971-06-17 | Verfahren zur Herstellung des neuen α-(p-Chlorphenoxy)-isobuttersäure-[2'-(p-Chlorphenoxy)-2'-methyl]-propylesters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702030003 DE2030003A1 (de) | 1970-06-18 | 1970-06-18 | alpha (p Chlor) phenoxy isobutter saure eckige Klammer auf 2 (p Chlor) 'phenoxy 2 methyl eckige Klammer zu propylester und Verfahren zur Herstel lung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2030003A1 true DE2030003A1 (de) | 1971-12-23 |
Family
ID=5774287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702030003 Pending DE2030003A1 (de) | 1970-06-18 | 1970-06-18 | alpha (p Chlor) phenoxy isobutter saure eckige Klammer auf 2 (p Chlor) 'phenoxy 2 methyl eckige Klammer zu propylester und Verfahren zur Herstel lung derselben |
Country Status (5)
-
1970
- 1970-06-18 DE DE19702030003 patent/DE2030003A1/de active Pending
-
1971
- 1971-06-15 CH CH872271A patent/CH557325A/xx not_active IP Right Cessation
- 1971-06-16 FR FR7121792A patent/FR2100774B1/fr not_active Expired
- 1971-06-16 GB GB1291010D patent/GB1291010A/en not_active Expired
- 1971-06-17 AT AT525371A patent/AT308081B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT308081B (de) | 1973-06-25 |
| FR2100774B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-17 |
| FR2100774A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-03-24 |
| CH557325A (de) | 1974-12-31 |
| GB1291010A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-27 |
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