IL44664A - Process for the manufacture of 7alpha beta-alkylhexahydro-5-oxo-4alpha-indanecarboxylic acid derivatives - Google Patents
Process for the manufacture of 7alpha beta-alkylhexahydro-5-oxo-4alpha-indanecarboxylic acid derivativesInfo
- Publication number
- IL44664A IL44664A IL44664A IL4466474A IL44664A IL 44664 A IL44664 A IL 44664A IL 44664 A IL44664 A IL 44664A IL 4466474 A IL4466474 A IL 4466474A IL 44664 A IL44664 A IL 44664A
- Authority
- IL
- Israel
- Prior art keywords
- group
- catalyst
- palladium
- carried out
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 29
- 239000002253 acid Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 229910021653 sulphate ion Inorganic materials 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- -1 formyloxy Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OMRDZQXXMYCHBU-UHFFFAOYSA-N ethanol;propan-1-ol Chemical compound CCO.CCCO OMRDZQXXMYCHBU-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/38—Unsaturated compounds containing keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2320285A DE2320285C2 (de) | 1973-04-18 | 1973-04-18 | Verfahren zur Herstellung von Bicycloalkan-Carbonsäuren |
| DE19742409597 DE2409597C2 (de) | 1974-02-25 | 1974-02-25 | Verfahren zur Herstellung von Bicycloalkan-Carbonsäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44664A0 IL44664A0 (en) | 1974-06-30 |
| IL44664A true IL44664A (en) | 1977-06-30 |
Family
ID=25765025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44664A IL44664A (en) | 1973-04-18 | 1974-04-18 | Process for the manufacture of 7alpha beta-alkylhexahydro-5-oxo-4alpha-indanecarboxylic acid derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4052447A (it) |
| AT (1) | AT329048B (it) |
| AU (1) | AU472240B2 (it) |
| BE (1) | BE813905A (it) |
| CH (1) | CH583167A5 (it) |
| CS (1) | CS168474B2 (it) |
| DK (1) | DK140339C (it) |
| ES (1) | ES425430A1 (it) |
| FR (1) | FR2226382B1 (it) |
| HU (1) | HU171183B (it) |
| IL (1) | IL44664A (it) |
| IT (1) | IT1064068B (it) |
| NL (1) | NL7405176A (it) |
| SE (1) | SE412904B (it) |
| YU (1) | YU107374A (it) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR81251E (fr) * | 1957-08-23 | 1963-08-23 | Rolland Lab A | Procédé de préparation d'acide bêta-cyclopentyl-acrylique |
| US3897460A (en) * | 1968-10-04 | 1975-07-29 | Hoffmann La Roche | 3{62 -Tertiarybutoxy-decahydro-benz{8 E{9 indenes |
-
1974
- 1974-04-11 CH CH509674A patent/CH583167A5/xx not_active IP Right Cessation
- 1974-04-16 DK DK207074A patent/DK140339C/da active
- 1974-04-17 HU HU74SC00000469A patent/HU171183B/hu unknown
- 1974-04-17 ES ES425430A patent/ES425430A1/es not_active Expired
- 1974-04-17 AT AT317174A patent/AT329048B/de not_active IP Right Cessation
- 1974-04-17 NL NL7405176A patent/NL7405176A/xx not_active Application Discontinuation
- 1974-04-17 CS CS2755A patent/CS168474B2/cs unknown
- 1974-04-17 SE SE7405150A patent/SE412904B/xx unknown
- 1974-04-17 IT IT21530/74A patent/IT1064068B/it active
- 1974-04-17 YU YU01073/74A patent/YU107374A/xx unknown
- 1974-04-18 FR FR7413495A patent/FR2226382B1/fr not_active Expired
- 1974-04-18 AU AU68014/74A patent/AU472240B2/en not_active Expired
- 1974-04-18 IL IL44664A patent/IL44664A/en unknown
- 1974-04-18 BE BE143367A patent/BE813905A/xx unknown
-
1975
- 1975-12-18 US US05/641,998 patent/US4052447A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1064068B (it) | 1985-02-18 |
| FR2226382B1 (it) | 1977-10-14 |
| DK140339B (da) | 1979-08-06 |
| HU171183B (hu) | 1977-11-28 |
| YU107374A (en) | 1982-05-31 |
| SE412904B (sv) | 1980-03-24 |
| ATA317174A (de) | 1975-07-15 |
| CH583167A5 (it) | 1976-12-31 |
| ES425430A1 (es) | 1976-06-01 |
| FR2226382A1 (it) | 1974-11-15 |
| DK140339C (da) | 1979-12-31 |
| AU472240B2 (en) | 1976-05-20 |
| AT329048B (de) | 1976-04-26 |
| NL7405176A (it) | 1974-10-22 |
| IL44664A0 (en) | 1974-06-30 |
| BE813905A (fr) | 1974-10-18 |
| AU6801474A (en) | 1975-10-23 |
| CS168474B2 (it) | 1976-06-29 |
| US4052447A (en) | 1977-10-04 |
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