SU492081A3 - Способ получени производных 2-(4-бифенилил)-тетрагидрофурана - Google Patents
Способ получени производных 2-(4-бифенилил)-тетрагидрофуранаInfo
- Publication number
- SU492081A3 SU492081A3 SU1959084A SU1959084A SU492081A3 SU 492081 A3 SU492081 A3 SU 492081A3 SU 1959084 A SU1959084 A SU 1959084A SU 1959084 A SU1959084 A SU 1959084A SU 492081 A3 SU492081 A3 SU 492081A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- biphenylyl
- tetrahydrofuran
- fluoro
- mol
- acid
- Prior art date
Links
- LVMCMBNBTAUNJH-UHFFFAOYSA-N 2-(4-phenylphenyl)oxolane Chemical class C1CCOC1C1=CC=C(C=2C=CC=CC=2)C=C1 LVMCMBNBTAUNJH-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 for example Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- LEMQXNZXEDGKKY-UHFFFAOYSA-N 1-(3-fluoro-4-phenylphenyl)butane-1,4-diol Chemical compound FC1=C(C=CC(=C1)C(CCCO)O)C1=CC=CC=C1 LEMQXNZXEDGKKY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Chemical class 0.000 description 3
- 239000012445 acidic reagent Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000007530 organic bases Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KUOBJVBOCPFTTF-UHFFFAOYSA-N 4-(4-phenylphenyl)but-3-en-1-ol Chemical class C1=CC(C=CCCO)=CC=C1C1=CC=CC=C1 KUOBJVBOCPFTTF-UHFFFAOYSA-N 0.000 description 1
- OFBMAASCQMDWRI-UHFFFAOYSA-N 4-(4-phenylphenyl)but-3-enoic acid Chemical class C1=CC(C=CCC(=O)O)=CC=C1C1=CC=CC=C1 OFBMAASCQMDWRI-UHFFFAOYSA-N 0.000 description 1
- RHLVAWHROJGHTG-UHFFFAOYSA-N 4-(4-phenylphenyl)butan-1-ol Chemical class C1=CC(CCCCO)=CC=C1C1=CC=CC=C1 RHLVAWHROJGHTG-UHFFFAOYSA-N 0.000 description 1
- NJGRSTRMISTCEB-UHFFFAOYSA-N 4-hydroxy-4-(4-phenylphenyl)butanoic acid Chemical class C1=CC(C(CCC(O)=O)O)=CC=C1C1=CC=CC=C1 NJGRSTRMISTCEB-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical class C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MSZYQCNHWFXSAK-UHFFFAOYSA-N oxolane;phosphoric acid Chemical compound C1CCOC1.OP(O)(O)=O MSZYQCNHWFXSAK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2240438A DE2240438A1 (de) | 1972-08-17 | 1972-08-17 | Neue 2-(4-biphenylyl)-tetrahydrofurane und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU492081A3 true SU492081A3 (ru) | 1975-11-15 |
Family
ID=5853787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1959084A SU492081A3 (ru) | 1972-08-17 | 1973-08-14 | Способ получени производных 2-(4-бифенилил)-тетрагидрофурана |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3901927A (en, 2012) |
| JP (1) | JPS49124055A (en, 2012) |
| AT (2) | AT324320B (en, 2012) |
| BE (1) | BE803731A (en, 2012) |
| BG (2) | BG20789A3 (en, 2012) |
| CA (1) | CA1010047A (en, 2012) |
| CH (1) | CH585741A5 (en, 2012) |
| DD (1) | DD109379A5 (en, 2012) |
| DE (1) | DE2240438A1 (en, 2012) |
| ES (1) | ES417881A1 (en, 2012) |
| FR (1) | FR2196169B1 (en, 2012) |
| GB (1) | GB1412663A (en, 2012) |
| HU (1) | HU166651B (en, 2012) |
| IL (1) | IL43000A (en, 2012) |
| NL (1) | NL7311296A (en, 2012) |
| PH (1) | PH9535A (en, 2012) |
| RO (2) | RO63767A (en, 2012) |
| SU (1) | SU492081A3 (en, 2012) |
| ZA (1) | ZA735627B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2850330A1 (de) * | 1977-12-01 | 1979-06-07 | Sandoz Ag | Verfahren zur herstellung von phenylbutenonen |
| US4918207A (en) * | 1988-03-30 | 1990-04-17 | Aldrich Chemical Co., Inc. | Novel optically active halo-substituted tetrahydrofurans |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2251835A (en) * | 1939-05-05 | 1941-08-05 | Gen Aniline & Film Corp | Production of tetrahydrofurane from 1,4-butylene glycol |
| BE790085A (fr) * | 1971-10-15 | 1973-04-13 | Thomae Gmbh Dr K | Nouveaux 4-(4-biphenylyl)-butanols |
| BE790086A (fr) * | 1971-10-15 | 1973-04-13 | Thomae Gmbh Dr K | Le 4-(4-biphenylyl)-1-butanol |
-
1972
- 1972-08-17 DE DE2240438A patent/DE2240438A1/de active Pending
-
1973
- 1973-08-13 US US387803A patent/US3901927A/en not_active Expired - Lifetime
- 1973-08-14 CH CH1170373A patent/CH585741A5/xx not_active IP Right Cessation
- 1973-08-14 AT AT679274A patent/AT324320B/de not_active IP Right Cessation
- 1973-08-14 SU SU1959084A patent/SU492081A3/ru active
- 1973-08-14 ES ES417881A patent/ES417881A1/es not_active Expired
- 1973-08-14 AT AT710673A patent/AT324319B/de not_active IP Right Cessation
- 1973-08-15 HU HUTO922A patent/HU166651B/hu unknown
- 1973-08-15 BG BG024325A patent/BG20789A3/xx unknown
- 1973-08-15 PH PH14916*UA patent/PH9535A/en unknown
- 1973-08-15 BG BG027021A patent/BG20579A3/xx unknown
- 1973-08-16 GB GB3884073A patent/GB1412663A/en not_active Expired
- 1973-08-16 NL NL7311296A patent/NL7311296A/xx unknown
- 1973-08-16 JP JP48092054A patent/JPS49124055A/ja active Pending
- 1973-08-16 CA CA179,009A patent/CA1010047A/en not_active Expired
- 1973-08-16 IL IL43000A patent/IL43000A/en unknown
- 1973-08-16 ZA ZA00735627A patent/ZA735627B/xx unknown
- 1973-08-17 DD DD172954A patent/DD109379A5/xx unknown
- 1973-08-17 FR FR7330077A patent/FR2196169B1/fr not_active Expired
- 1973-08-17 BE BE134688A patent/BE803731A/xx unknown
- 1973-08-17 RO RO7300080999A patent/RO63767A/ro unknown
- 1973-08-17 RO RO7300075820A patent/RO63669A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO63669A (fr) | 1978-10-15 |
| BG20579A3 (bg) | 1975-12-05 |
| AU5930673A (en) | 1975-02-20 |
| NL7311296A (en, 2012) | 1974-02-19 |
| AT324320B (de) | 1975-08-25 |
| JPS49124055A (en, 2012) | 1974-11-27 |
| GB1412663A (en) | 1975-11-05 |
| IL43000A (en) | 1976-08-31 |
| BE803731A (fr) | 1974-02-18 |
| ES417881A1 (es) | 1976-06-16 |
| FR2196169A1 (en, 2012) | 1974-03-15 |
| FR2196169B1 (en, 2012) | 1977-04-15 |
| CH585741A5 (en, 2012) | 1977-03-15 |
| IL43000A0 (en) | 1973-11-28 |
| DE2240438A1 (de) | 1974-02-28 |
| HU166651B (en, 2012) | 1975-04-28 |
| PH9535A (en) | 1976-01-09 |
| AT324319B (de) | 1975-08-25 |
| DD109379A5 (en, 2012) | 1974-11-05 |
| US3901927A (en) | 1975-08-26 |
| CA1010047A (en) | 1977-05-10 |
| BG20789A3 (bg) | 1975-12-20 |
| ZA735627B (en) | 1976-01-28 |
| RO63767A (fr) | 1978-12-15 |
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