DE1144289B - 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
- DE1144289B DE1144289B DEF32051A DEF0032051A DE1144289B DE 1144289 B DE1144289 B DE 1144289B DE F32051 A DEF32051 A DE F32051A DE F0032051 A DEF0032051 A DE F0032051A DE 1144289 B DE1144289 B DE 1144289B
- Authority
- DE
- Germany
- Prior art keywords
- spiro
- oxo
- cyclohexane
- carboxylic acid
- cycloalkane
- 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 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 20
- 229910015900 BF3 Inorganic materials 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- -1 1- (3 ', 5' - di - n - propoxy - phenoxy) cyclohexane - 1 - carboxylic acid Chemical compound 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
- 239000000155 melt Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- MYGOJEJQUSAHHP-UHFFFAOYSA-N 1-(3,5-dimethoxyphenoxy)cyclopentane-1-carboxylic acid Chemical compound COC1=CC(OC)=CC(OC2(CCCC2)C(O)=O)=C1 MYGOJEJQUSAHHP-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- UMYQOSISRNJTPL-UHFFFAOYSA-N COC1=CC(OC2(CCC(C)CC2)C(O)=O)=CC(OC)=C1 Chemical compound COC1=CC(OC2(CCC(C)CC2)C(O)=O)=CC(OC)=C1 UMYQOSISRNJTPL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000047 product Substances 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
- 239000012265 solid product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- 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
- MGKPCLNUSDGXGT-UHFFFAOYSA-N 1-benzofuran-3-one Chemical compound C1=CC=C2C(=O)COC2=C1 MGKPCLNUSDGXGT-UHFFFAOYSA-N 0.000 description 1
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D59/00—Self-acting brakes, e.g. coming into operation at a predetermined speed
- F16D59/02—Self-acting brakes, e.g. coming into operation at a predetermined speed spring-loaded and adapted to be released by mechanical, fluid, or electromagnetic means
-
- 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)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Mechanical Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32051A DE1144289B (de) | 1960-09-06 | 1960-09-06 | Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1', 2-cumaranen) |
| CH432261A CH403793A (de) | 1960-04-14 | 1961-04-12 | Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1',2-cumaranen) |
| BE602608A BE602608A (fr) | 1960-04-14 | 1961-04-14 | 3-oxo-spiro-cycloalcane-1'.2-coumaranes et leur préparation |
| GB1362361A GB974896A (en) | 1960-04-14 | 1961-04-14 | 3-oxo-spiro-(cycloalkane-1:2-coumarans) and process of preparing them |
| NL6409817A NL6409817A (enrdf_load_stackoverflow) | 1960-09-06 | 1964-08-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32051A DE1144289B (de) | 1960-09-06 | 1960-09-06 | Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1', 2-cumaranen) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1144289B true DE1144289B (de) | 1963-02-28 |
Family
ID=7094470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF32051A Pending DE1144289B (de) | 1960-04-14 | 1960-09-06 | Verfahren zur Herstellung von 3-Oxo-spiro-(cycloalkan-1', 2-cumaranen) |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1144289B (enrdf_load_stackoverflow) |
| NL (1) | NL6409817A (enrdf_load_stackoverflow) |
-
1960
- 1960-09-06 DE DEF32051A patent/DE1144289B/de active Pending
-
1964
- 1964-08-25 NL NL6409817A patent/NL6409817A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6409817A (enrdf_load_stackoverflow) | 1964-11-25 |
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