SU359807A1 - - Google Patents
Info
- Publication number
- SU359807A1 SU359807A1 SU1615381A SU1615381A SU359807A1 SU 359807 A1 SU359807 A1 SU 359807A1 SU 1615381 A SU1615381 A SU 1615381A SU 1615381 A SU1615381 A SU 1615381A SU 359807 A1 SU359807 A1 SU 359807A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydroxy
- solution
- diethyl ether
- cyclopentyl
- added
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 126
- 239000000243 solution Substances 0.000 description 61
- 229960004132 diethyl ether Drugs 0.000 description 48
- 239000000203 mixture Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000010410 layer Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- -1 ethylene, epoxyethylene Chemical group 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000012259 ether extract Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 239000001187 sodium carbonate Substances 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 150000001940 cyclopentanes Chemical class 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000002378 acidificating Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- MWFMGBPGAXYFAR-UHFFFAOYSA-N Acetone cyanohydrin Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 4
- 239000003810 Jones reagent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 150000001844 chromium Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WDCKVVCOPDJIIB-UHFFFAOYSA-N 2-(7-hydroxyheptyl)cyclopent-2-en-1-one Chemical compound OCCCCCCCC1=CCCC1=O WDCKVVCOPDJIIB-UHFFFAOYSA-N 0.000 description 3
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 150000002081 enamines Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000003638 reducing agent Substances 0.000 description 3
- VSMOENVRRABVKN-UHFFFAOYSA-N 1-Octen-3-ol Chemical compound CCCCCC(O)C=C VSMOENVRRABVKN-UHFFFAOYSA-N 0.000 description 2
- DGLJOSHQJSIUFP-UHFFFAOYSA-N 1-[3-hydroxy-2-(7-hydroxyheptyl)cyclopentyl]oct-1-en-3-one Chemical compound CCCCCC(=O)C=CC1CCC(O)C1CCCCCCCO DGLJOSHQJSIUFP-UHFFFAOYSA-N 0.000 description 2
- FCBDNJCPZBFBPE-UHFFFAOYSA-N 2-(7-hydroxyheptyl)-3-oxocyclopentane-1-carbonitrile Chemical compound OCCCCCCCC1C(C#N)CCC1=O FCBDNJCPZBFBPE-UHFFFAOYSA-N 0.000 description 2
- SBABSRXGDTVMAF-UHFFFAOYSA-N 2-(7-hydroxyheptyl)-4-methyl-3-oxocyclopentane-1-carbonitrile Chemical compound CC1CC(C#N)C(CCCCCCCO)C1=O SBABSRXGDTVMAF-UHFFFAOYSA-N 0.000 description 2
- AMEQIIYEGPCAKB-UHFFFAOYSA-N 7-(oxan-2-yloxy)heptanal Chemical compound O=CCCCCCCOC1CCCCO1 AMEQIIYEGPCAKB-UHFFFAOYSA-N 0.000 description 2
- AMODMEKOXAVCIV-UHFFFAOYSA-N CC1CC(C=O)C(CCCCCCCO)C1O Chemical compound CC1CC(C=O)C(CCCCCCCO)C1O AMODMEKOXAVCIV-UHFFFAOYSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004980 cyclopropylene group Chemical group 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229940113083 morpholine Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- VESKWLIOIKZSNK-UHFFFAOYSA-N 1-[3-hydroxy-2-(6-hydroxyhexyl)cyclopentyl]oct-1-en-3-one Chemical compound CCCCCC(=O)C=CC1CCC(O)C1CCCCCCO VESKWLIOIKZSNK-UHFFFAOYSA-N 0.000 description 1
- HDJAHLMRRVIUTD-UHFFFAOYSA-N 1-[3-hydroxy-2-(7-hydroxyheptyl)-4-methylcyclopentyl]oct-1-en-3-one Chemical compound CCCCCC(=O)C=CC1CC(C)C(O)C1CCCCCCCO HDJAHLMRRVIUTD-UHFFFAOYSA-N 0.000 description 1
- SVPIOJVFZDVVRV-UHFFFAOYSA-N 1-[3-hydroxy-4-(7-hydroxyheptyl)-2-methylcyclopentyl]oct-1-en-3-one Chemical compound CCCCCC(=O)C=CC1CC(CCCCCCCO)C(O)C1C SVPIOJVFZDVVRV-UHFFFAOYSA-N 0.000 description 1
- GYMSYKZTGSJZGX-UHFFFAOYSA-N 2-(6-hydroxyhexyl)-3-oxocyclopentane-1-carbonitrile Chemical compound OCCCCCCC1C(C#N)CCC1=O GYMSYKZTGSJZGX-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-Chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- PGJVCEYNLIWQJR-UHFFFAOYSA-N 2-cyclopentylheptanoic acid Chemical compound CCCCCC(C(O)=O)C1CCCC1 PGJVCEYNLIWQJR-UHFFFAOYSA-N 0.000 description 1
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 1
- PLVOWOHSFJLXOR-UHFFFAOYSA-N 2-pentylheptanoic acid Chemical compound CCCCCC(C(O)=O)CCCCC PLVOWOHSFJLXOR-UHFFFAOYSA-N 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- WQRWPJHHGRWEPZ-UHFFFAOYSA-N 3-hydroxy-2-(6-hydroxyhexyl)cyclopentane-1-carbaldehyde Chemical compound OCCCCCCC1C(O)CCC1C=O WQRWPJHHGRWEPZ-UHFFFAOYSA-N 0.000 description 1
- WULIZEOAYMSIHS-UHFFFAOYSA-N 4-chloro-5-methylpyrrolo[3,2-d]pyrimidine-6-carbaldehyde Chemical compound C1=NC(Cl)=C2N(C)C(C=O)=CC2=N1 WULIZEOAYMSIHS-UHFFFAOYSA-N 0.000 description 1
- UVZRWXWWEMRURR-UHFFFAOYSA-N 6-(cyclopenten-1-yl)hexan-1-ol Chemical compound OCCCCCCC1=CCCC1 UVZRWXWWEMRURR-UHFFFAOYSA-N 0.000 description 1
- PRGUNFCZRODZGQ-UHFFFAOYSA-N 6-(oxan-2-yloxy)hexanal Chemical compound O=CCCCCCOC1CCCCO1 PRGUNFCZRODZGQ-UHFFFAOYSA-N 0.000 description 1
- CQRYUGPAMSWZHT-UHFFFAOYSA-N CC(C(=O)O)(CCCCC)C1CCCC1 Chemical compound CC(C(=O)O)(CCCCC)C1CCCC1 CQRYUGPAMSWZHT-UHFFFAOYSA-N 0.000 description 1
- LQIIEHBULBHJKX-UHFFFAOYSA-N CC(C)C[AlH2] Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 1
- JDMRFNAGZCVIFZ-UHFFFAOYSA-N CC1=CCC(CCCCCCCO)C1=O Chemical compound CC1=CCC(CCCCCCCO)C1=O JDMRFNAGZCVIFZ-UHFFFAOYSA-N 0.000 description 1
- QWDYWVFPKNKHOK-UHFFFAOYSA-N CC1C(C#N)CC(CCCCCCCO)C1=O Chemical compound CC1C(C#N)CC(CCCCCCCO)C1=O QWDYWVFPKNKHOK-UHFFFAOYSA-N 0.000 description 1
- AMIUCPXBBSPWEL-UHFFFAOYSA-N CC1C(O)C(CCCCCCCO)CC1C=O Chemical compound CC1C(O)C(CCCCCCCO)CC1C=O AMIUCPXBBSPWEL-UHFFFAOYSA-N 0.000 description 1
- PGGHZCZHMCXSHW-UHFFFAOYSA-N CC1CC=C(CCCCCCCO)C1=O Chemical compound CC1CC=C(CCCCCCCO)C1=O PGGHZCZHMCXSHW-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N Cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N Cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 1
- 241000406668 Loxodonta cyclotis Species 0.000 description 1
- 229910004664 ORa Inorganic materials 0.000 description 1
- 241000658540 Ora Species 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241001000594 Tanna Species 0.000 description 1
- 241000278713 Theora Species 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N Triphenylphosphine oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical compound [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU359807A1 true SU359807A1 (de) |
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