FR2479822A1 - Glycidylethers d'alcools utiles comme intermediaires de synthese et leur procede de preparation - Google Patents
Glycidylethers d'alcools utiles comme intermediaires de synthese et leur procede de preparation Download PDFInfo
- Publication number
- FR2479822A1 FR2479822A1 FR8007716A FR8007716A FR2479822A1 FR 2479822 A1 FR2479822 A1 FR 2479822A1 FR 8007716 A FR8007716 A FR 8007716A FR 8007716 A FR8007716 A FR 8007716A FR 2479822 A1 FR2479822 A1 FR 2479822A1
- Authority
- FR
- France
- Prior art keywords
- sep
- epoxypropane
- propane
- epoxy
- radical
- 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.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000543 intermediate Substances 0.000 title description 3
- 125000001931 aliphatic group Chemical group 0.000 title description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 title description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 title description 2
- 239000002876 beta blocker Substances 0.000 title 1
- 229940097320 beta blocking agent Drugs 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- -1 cyclohexen-3-yloxy Chemical group 0.000 claims description 47
- 239000001294 propane Substances 0.000 claims description 22
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 2
- VIVJQHRQMZMPND-UHFFFAOYSA-N 1-[2-(oxiran-2-ylmethoxy)ethyl]piperidine Chemical compound C(C1CO1)OCCN1CCCCC1 VIVJQHRQMZMPND-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- STKPOFHDVPPKEF-UHFFFAOYSA-N 4-[2-(oxiran-2-ylmethoxy)ethyl]morpholine Chemical compound C(C1CO1)OCCN1CCOCC1 STKPOFHDVPPKEF-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 abstract description 21
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 150000001723 carbon free-radicals Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- UWBBAKWAAWCHSZ-UHFFFAOYSA-N 3-phenylprop-1-en-2-ol Chemical compound OC(=C)CC1=CC=CC=C1 UWBBAKWAAWCHSZ-UHFFFAOYSA-N 0.000 description 1
- 241000928106 Alain Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8007716A FR2479822A1 (fr) | 1980-04-04 | 1980-04-04 | Glycidylethers d'alcools utiles comme intermediaires de synthese et leur procede de preparation |
| ES500979A ES8202547A1 (es) | 1980-04-04 | 1981-04-01 | Procedimiento de preparar glicidil eteres de alcoholes |
| NL8101658A NL8101658A (nl) | 1980-04-04 | 1981-04-02 | Werkwijze voor het bereiden van glycidylethers van primaire en secundaire alcoholen en de toepassing daarvan als synthesetussenprodukten in de farmaceutische industrie. |
| IT67468/81A IT1144326B (it) | 1980-04-04 | 1981-04-03 | Glicidil eteri di alcoli particolarmente utili come intermedi per la sintesi di prodotti farmaceutici e procedimento per la loro preparazione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8007716A FR2479822A1 (fr) | 1980-04-04 | 1980-04-04 | Glycidylethers d'alcools utiles comme intermediaires de synthese et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2479822A1 true FR2479822A1 (fr) | 1981-10-09 |
| FR2479822B1 FR2479822B1 (enrdf_load_stackoverflow) | 1983-07-29 |
Family
ID=9240573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8007716A Granted FR2479822A1 (fr) | 1980-04-04 | 1980-04-04 | Glycidylethers d'alcools utiles comme intermediaires de synthese et leur procede de preparation |
Country Status (4)
| Country | Link |
|---|---|
| ES (1) | ES8202547A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2479822A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1144326B (enrdf_load_stackoverflow) |
| NL (1) | NL8101658A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087708A (en) * | 1990-03-27 | 1992-02-11 | Deutsche Solvay-Werke Gmbh | Method of preparing 2,2-dimethyl-4-(2',3'-epoxy) propoxymethyl-1,3-dioxolane and use thereof |
| EP1201635A1 (en) * | 2000-10-23 | 2002-05-02 | Takasago International Corporation | Process for producing 3-l-menthoxypropane-1,2-diol |
| US6515188B2 (en) | 2001-04-23 | 2003-02-04 | Takasago International Corporation | Method for producing 3-l-menthoxypropane-1,2-diol |
| CN117304140A (zh) * | 2023-08-24 | 2023-12-29 | 浦拉司科技（上海）有限责任公司 | 一种4-联苯甲基缩水甘油醚的制备方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4623701A (en) | 1985-07-10 | 1986-11-18 | The Dow Chemical Company | Multifunctional epoxy resins |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1552851A (enrdf_load_stackoverflow) * | 1966-07-21 | 1969-01-10 | Boehringer Mannheim Gmbh |
-
1980
- 1980-04-04 FR FR8007716A patent/FR2479822A1/fr active Granted
-
1981
- 1981-04-01 ES ES500979A patent/ES8202547A1/es not_active Expired
- 1981-04-02 NL NL8101658A patent/NL8101658A/nl not_active Application Discontinuation
- 1981-04-03 IT IT67468/81A patent/IT1144326B/it active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1552851A (enrdf_load_stackoverflow) * | 1966-07-21 | 1969-01-10 | Boehringer Mannheim Gmbh |
Non-Patent Citations (3)
| Title |
|---|
| CA1970 * |
| CA1976 * |
| EXBK/65 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087708A (en) * | 1990-03-27 | 1992-02-11 | Deutsche Solvay-Werke Gmbh | Method of preparing 2,2-dimethyl-4-(2',3'-epoxy) propoxymethyl-1,3-dioxolane and use thereof |
| EP1201635A1 (en) * | 2000-10-23 | 2002-05-02 | Takasago International Corporation | Process for producing 3-l-menthoxypropane-1,2-diol |
| US6407293B1 (en) | 2000-10-23 | 2002-06-18 | Takasago International Corporation | Process for producing 3-1-menthoxypropane-1,2-diol |
| US6515188B2 (en) | 2001-04-23 | 2003-02-04 | Takasago International Corporation | Method for producing 3-l-menthoxypropane-1,2-diol |
| CN117304140A (zh) * | 2023-08-24 | 2023-12-29 | 浦拉司科技（上海）有限责任公司 | 一种4-联苯甲基缩水甘油醚的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1144326B (it) | 1986-10-29 |
| FR2479822B1 (enrdf_load_stackoverflow) | 1983-07-29 |
| ES500979A0 (es) | 1982-02-16 |
| NL8101658A (nl) | 1981-11-02 |
| IT8167468A0 (it) | 1981-04-03 |
| ES8202547A1 (es) | 1982-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |