JPS6320412B2 - - Google Patents
Info
- Publication number
- JPS6320412B2 JPS6320412B2 JP14078780A JP14078780A JPS6320412B2 JP S6320412 B2 JPS6320412 B2 JP S6320412B2 JP 14078780 A JP14078780 A JP 14078780A JP 14078780 A JP14078780 A JP 14078780A JP S6320412 B2 JPS6320412 B2 JP S6320412B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- reaction
- lower alkyl
- formula
- represented
- 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.)
- Expired
Links
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- LUTDLYPHDVQSHT-UHFFFAOYSA-N 2-hydroxycyclopentan-1-one Chemical class OC1CCCC1=O LUTDLYPHDVQSHT-UHFFFAOYSA-N 0.000 claims description 6
- WOPKYMRPOKFYNI-UHFFFAOYSA-N 2-hydroxycyclopent-2-en-1-one Chemical compound OC1=CCCC1=O WOPKYMRPOKFYNI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002994 raw material Substances 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 239000011981 lindlar catalyst Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 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 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- -1 2-(2-trans-pentenyl)-3-hydroxy-3-methylcyclopentanone Chemical compound 0.000 description 1
- UHDNWEAUYCDSFH-UHFFFAOYSA-N 3-hydroxy-3-methyl-2-propylcyclopentan-1-one Chemical compound CCCC1C(=O)CCC1(C)O UHDNWEAUYCDSFH-UHFFFAOYSA-N 0.000 description 1
- ZLKSWXWJGSKXGZ-WAYWQWQTSA-N 4-hydroxy-4-methyl-5-[(z)-pent-1-enyl]cyclopent-2-en-1-one Chemical compound CCC\C=C/C1C(=O)C=CC1(C)O ZLKSWXWJGSKXGZ-WAYWQWQTSA-N 0.000 description 1
- GRDMLYFTFVGTIH-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-pent-2-ynylcyclopent-2-en-1-one Chemical compound CCC#CCC1C(=O)C=CC1(C)O GRDMLYFTFVGTIH-UHFFFAOYSA-N 0.000 description 1
- HNNRFEWGWVQYNP-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1(O)C=CC(=O)C1CC=C HNNRFEWGWVQYNP-UHFFFAOYSA-N 0.000 description 1
- IKVJOBDPGRWXRL-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-propylcyclopent-2-en-1-one Chemical compound CCCC1C(=O)C=CC1(C)O IKVJOBDPGRWXRL-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- QTRVNOROFFZSJJ-WAYWQWQTSA-N C(=C/CCC)/C1C(CCC1(C)O)=O Chemical compound C(=C/CCC)/C1C(CCC1(C)O)=O QTRVNOROFFZSJJ-WAYWQWQTSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 1
- 229910000003 Lead carbonate Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical class OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229940112735 lead carbonate Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 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
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14078780A JPS5764635A (en) | 1980-10-07 | 1980-10-07 | Hydroxycyclopentanone and its preparation |
| CH3765/81A CH648282A5 (de) | 1980-06-10 | 1981-06-09 | Verfahren zur herstellung von oxocyclopentenen. |
| FR8111320A FR2498592A1 (fr) | 1980-06-10 | 1981-06-09 | Procede de preparation de derives d'oxocyclopentene et nouveaux produits ainsi obtenus |
| DE19813122995 DE3122995A1 (de) | 1980-06-10 | 1981-06-10 | Verfahren zur herstellung von oxocyclopentenen |
| DE3153651A DE3153651C2 (de) | 1980-06-10 | 1981-06-10 | |
| FR8117412A FR2485520A1 (fr) | 1980-06-10 | 1981-09-15 | Hydroxycyclopentanones substituees |
| US06/831,067 US4970345A (en) | 1980-06-10 | 1986-02-20 | Process for preparing oxocyclopentene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14078780A JPS5764635A (en) | 1980-10-07 | 1980-10-07 | Hydroxycyclopentanone and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5764635A JPS5764635A (en) | 1982-04-19 |
| JPS6320412B2 true JPS6320412B2 (de) | 1988-04-27 |
Family
ID=15276725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14078780A Granted JPS5764635A (en) | 1980-06-10 | 1980-10-07 | Hydroxycyclopentanone and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5764635A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04500583A (ja) * | 1988-10-14 | 1992-01-30 | オックスフォード メディカル リミテッド | 磁界発生組成体及び方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017031271A (ja) * | 2015-07-30 | 2017-02-09 | 東レフィルム加工株式会社 | コーティングフィルム |
-
1980
- 1980-10-07 JP JP14078780A patent/JPS5764635A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04500583A (ja) * | 1988-10-14 | 1992-01-30 | オックスフォード メディカル リミテッド | 磁界発生組成体及び方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5764635A (en) | 1982-04-19 |
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