CH403793A - Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1',2-cumaranen) - Google Patents
Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1',2-cumaranen)Info
- Publication number
- CH403793A CH403793A CH432261A CH432261A CH403793A CH 403793 A CH403793 A CH 403793A CH 432261 A CH432261 A CH 432261A CH 432261 A CH432261 A CH 432261A CH 403793 A CH403793 A CH 403793A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclohexane
- spiro
- oxo
- ether
- cyclohexan
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 33
- 238000002360 preparation method Methods 0.000 title claims description 9
- 229910015900 BF3 Inorganic materials 0.000 claims description 27
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 27
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 108
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 63
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- -1 methoxy, ethoxy, n-propoxy, n-butoxy Chemical group 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 235000011118 potassium hydroxide Nutrition 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- XQDNFAMOIPNVES-UHFFFAOYSA-N 3,5-Dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1 XQDNFAMOIPNVES-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000155 melt Substances 0.000 description 11
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 9
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
- LFZSCVPLZJRMIL-UHFFFAOYSA-N C(C)OC=1C=C(OC2(CCCCC2)C(=O)O)C=C(C=1)OCC Chemical compound C(C)OC=1C=C(OC2(CCCCC2)C(=O)O)C=C(C=1)OCC LFZSCVPLZJRMIL-UHFFFAOYSA-N 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000010907 mechanical stirring Methods 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- BFFKHFHNXVCTKK-UHFFFAOYSA-N 1-(3,5-dimethoxyphenoxy)-4-methoxycyclohexane-1-carboxylic acid Chemical compound COC=1C=C(OC2(CCC(CC2)OC)C(=O)O)C=C(C1)OC BFFKHFHNXVCTKK-UHFFFAOYSA-N 0.000 description 4
- PBYPBMHUTLMVRS-UHFFFAOYSA-N 1-(trichloromethyl)cyclohexan-1-ol Chemical compound ClC(Cl)(Cl)C1(O)CCCCC1 PBYPBMHUTLMVRS-UHFFFAOYSA-N 0.000 description 4
- MMYNAOPNOXGWSK-UHFFFAOYSA-N 2-methoxy-1-(trichloromethyl)cyclohexan-1-ol Chemical compound COC1CCCCC1(O)C(Cl)(Cl)Cl MMYNAOPNOXGWSK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QMJWDFUMQIPGOV-UHFFFAOYSA-N 1-(2-chloro-3,5-dimethoxyphenoxy)cyclohexane-1-carboxylic acid Chemical compound COC=1C=C(OC2(CCCCC2)C(=O)O)C(=C(C1)OC)Cl QMJWDFUMQIPGOV-UHFFFAOYSA-N 0.000 description 3
- KRPCSMVPNXVPNC-UHFFFAOYSA-N 1-(3,5-dimethoxyphenoxy)-4-(2,4,4-trimethylpentan-2-yl)cyclohexane-1-carboxylic acid Chemical compound COC=1C=C(OC2(CCC(CC2)C(CC(C)(C)C)(C)C)C(=O)O)C=C(C1)OC KRPCSMVPNXVPNC-UHFFFAOYSA-N 0.000 description 3
- XNLZPQBTSKYBTB-UHFFFAOYSA-N 1-(3,5-dimethoxyphenoxy)cyclohexane-1-carboxylic acid Chemical compound COC=1C=C(OC2(CCCCC2)C(=O)O)C=C(C1)OC XNLZPQBTSKYBTB-UHFFFAOYSA-N 0.000 description 3
- RGFIOPMGYXCIKT-UHFFFAOYSA-N 1-(trichloromethyl)-4-(2,4,4-trimethylpentan-2-yl)cyclohexan-1-ol Chemical compound ClC(C1(CCC(CC1)C(CC(C)(C)C)(C)C)O)(Cl)Cl RGFIOPMGYXCIKT-UHFFFAOYSA-N 0.000 description 3
- FMHHCUBLAXNVHV-UHFFFAOYSA-N 4-chloro-3,5-dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1Cl FMHHCUBLAXNVHV-UHFFFAOYSA-N 0.000 description 3
- WLRUQPFHEBOYOV-UHFFFAOYSA-N 4-ethyl-1-(trichloromethyl)cyclohexan-1-ol Chemical compound C(C)C1CCC(CC1)(O)C(Cl)(Cl)Cl WLRUQPFHEBOYOV-UHFFFAOYSA-N 0.000 description 3
- OZYCTWGJIAKBCH-UHFFFAOYSA-N 4-methoxy-1-(trichloromethyl)cyclohexan-1-ol Chemical compound COC1CCC(O)(CC1)C(Cl)(Cl)Cl OZYCTWGJIAKBCH-UHFFFAOYSA-N 0.000 description 3
- 241001480043 Arthrodermataceae Species 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 229940121375 antifungal agent Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000037304 dermatophytes Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- OTYDNPARSNXLKJ-UHFFFAOYSA-N 1-(3,5-dimethoxyphenoxy)-2-methoxycyclohexane-1-carboxylic acid Chemical compound COC=1C=C(OC2(C(CCCC2)OC)C(=O)O)C=C(C1)OC OTYDNPARSNXLKJ-UHFFFAOYSA-N 0.000 description 2
- SCGUCUCMGMIQLG-UHFFFAOYSA-N 1-(3,5-dimethoxyphenoxy)-4-ethylcyclohexane-1-carboxylic acid Chemical compound COC=1C=C(OC2(CCC(CC2)CC)C(=O)O)C=C(C1)OC SCGUCUCMGMIQLG-UHFFFAOYSA-N 0.000 description 2
- WJHUEROGLDPWKN-UHFFFAOYSA-N 1-(4-chloro-3,5-dimethoxyphenoxy)-4-ethoxycyclohexane-1-carboxylic acid Chemical compound COC=1C=C(OC2(CCC(CC2)OCC)C(=O)O)C=C(C1Cl)OC WJHUEROGLDPWKN-UHFFFAOYSA-N 0.000 description 2
- HJXIDGGCRTZQJL-UHFFFAOYSA-N 1-(trichloromethyl)cyclopentan-1-ol Chemical compound ClC(Cl)(Cl)C1(O)CCCC1 HJXIDGGCRTZQJL-UHFFFAOYSA-N 0.000 description 2
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 2
- DAOITXVOWFEFKZ-UHFFFAOYSA-N 2-bromo-3,5-dimethoxyphenol Chemical compound COC1=CC(O)=C(Br)C(OC)=C1 DAOITXVOWFEFKZ-UHFFFAOYSA-N 0.000 description 2
- UXZNREKNBHZYIT-UHFFFAOYSA-N 2-chloro-3,5-dimethoxyphenol Chemical compound COC1=CC(O)=C(Cl)C(OC)=C1 UXZNREKNBHZYIT-UHFFFAOYSA-N 0.000 description 2
- YLMYXAAUQOWAOK-UHFFFAOYSA-N 3,5-diethoxyphenol Chemical compound CCOC1=CC(O)=CC(OCC)=C1 YLMYXAAUQOWAOK-UHFFFAOYSA-N 0.000 description 2
- WBFJYRIXOUDZDJ-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)cyclohexan-1-one Chemical compound CC(C)(C)CC(C)(C)C1CCC(=O)CC1 WBFJYRIXOUDZDJ-UHFFFAOYSA-N 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VATYKBZLUDXTDU-UHFFFAOYSA-N COC(CCCC1)C1(C(O)=O)OC1=CC(OC)=CC(OC)=C1Cl Chemical compound COC(CCCC1)C1(C(O)=O)OC1=CC(OC)=CC(OC)=C1Cl VATYKBZLUDXTDU-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 2
- 230000001857 anti-mycotic effect Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
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- 238000001665 trituration Methods 0.000 description 2
- VDHKOXQMVGLFEB-UHFFFAOYSA-N 1-(2-bromo-3,5-dimethoxyphenoxy)cyclohexane-1-carboxylic acid Chemical compound BrC1=C(C=C(C=C1OC1(CCCCC1)C(=O)O)OC)OC VDHKOXQMVGLFEB-UHFFFAOYSA-N 0.000 description 1
- WPEDSSOMUSIGJF-UHFFFAOYSA-N 1-(3,5-dimethoxyphenoxy)cyclohexane-1-carbonyl chloride Chemical compound COC=1C=C(OC2(CCCCC2)C(=O)Cl)C=C(C=1)OC WPEDSSOMUSIGJF-UHFFFAOYSA-N 0.000 description 1
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- AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 1
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- AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment 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
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009183 running Effects 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
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31001A DE1145180B (de) | 1960-04-14 | 1960-04-14 | Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1',2-cumaranen |
| DEF32051A DE1144289B (de) | 1960-09-06 | 1960-09-06 | Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1', 2-cumaranen) |
| DEF32115A DE1160448B (de) | 1960-09-14 | 1960-09-14 | Verfahren zur Herstellung von 3-Oxo-spiro-(cyclohexan-1', 2-cumaranen) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH403793A true CH403793A (de) | 1965-12-15 |
Family
ID=27210171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH432261A CH403793A (de) | 1960-04-14 | 1961-04-12 | Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1',2-cumaranen) |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE602608A (fr) |
| CH (1) | CH403793A (fr) |
| GB (1) | GB974896A (fr) |
-
1961
- 1961-04-12 CH CH432261A patent/CH403793A/de unknown
- 1961-04-14 BE BE602608A patent/BE602608A/fr unknown
- 1961-04-14 GB GB1362361A patent/GB974896A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE602608A (fr) | 1961-10-16 |
| GB974896A (en) | 1964-11-11 |
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