JPS6316365B2 - - Google Patents
Info
- Publication number
- JPS6316365B2 JPS6316365B2 JP56127224A JP12722481A JPS6316365B2 JP S6316365 B2 JPS6316365 B2 JP S6316365B2 JP 56127224 A JP56127224 A JP 56127224A JP 12722481 A JP12722481 A JP 12722481A JP S6316365 B2 JPS6316365 B2 JP S6316365B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- tetrahydronaphthalene
- reaction
- pentamethyl
- optically active
- 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
- 239000003054 catalyst Substances 0.000 claims description 10
- JMLRZDXOJMFVPB-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydronaphthalen-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)CCCC2=C1 JMLRZDXOJMFVPB-UHFFFAOYSA-N 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- -1 lithium aluminum hydride Chemical compound 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 description 6
- 239000010446 mirabilite Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 3
- 229910000103 lithium hydride Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- ZEUZBDYJXCWXAT-ZDUSSCGKSA-N 2-[(2r)-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalen-2-yl]ethanol Chemical compound C([C@H](CCO)C1(C)C)C(C)(C)C=2C1=CC(C)=CC=2 ZEUZBDYJXCWXAT-ZDUSSCGKSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- HVORSWUYOJYJQI-ZDUSSCGKSA-N (2S)-2-ethyl-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalene Chemical compound C1=C(C)C=C2C(C)(C)[C@@H](CC)CC(C)(C)C2=C1 HVORSWUYOJYJQI-ZDUSSCGKSA-N 0.000 description 1
- JXAAVJDHADIFMU-ZDUSSCGKSA-N (2r)-2-(2-chloroethyl)-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalene Chemical compound C([C@H](CCCl)C1(C)C)C(C)(C)C=2C1=CC(C)=CC=2 JXAAVJDHADIFMU-ZDUSSCGKSA-N 0.000 description 1
- HVORSWUYOJYJQI-CYBMUJFWSA-N (2r)-2-ethyl-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalene Chemical compound C1=C(C)C=C2C(C)(C)[C@H](CC)CC(C)(C)C2=C1 HVORSWUYOJYJQI-CYBMUJFWSA-N 0.000 description 1
- JXAAVJDHADIFMU-CYBMUJFWSA-N (2s)-2-(2-chloroethyl)-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalene Chemical compound C([C@@H](CCCl)C1(C)C)C(C)(C)C=2C1=CC(C)=CC=2 JXAAVJDHADIFMU-CYBMUJFWSA-N 0.000 description 1
- IEBXZRQOXHLIGF-QMMMGPOBSA-N (4r)-5,5-dimethyl-4-(2-methylprop-1-enyl)oxolan-2-one Chemical compound CC(C)=C[C@H]1CC(=O)OC1(C)C IEBXZRQOXHLIGF-QMMMGPOBSA-N 0.000 description 1
- IEBXZRQOXHLIGF-MRVPVSSYSA-N (4s)-5,5-dimethyl-4-(2-methylprop-1-enyl)oxolan-2-one Chemical compound CC(C)=C[C@@H]1CC(=O)OC1(C)C IEBXZRQOXHLIGF-MRVPVSSYSA-N 0.000 description 1
- AZRHCOAXTMKTDJ-CQSZACIVSA-N (4s)-5,5-dimethyl-4-[2-methyl-2-(4-methylphenyl)propyl]oxolan-2-one Chemical compound C1=CC(C)=CC=C1C(C)(C)C[C@@H]1C(C)(C)OC(=O)C1 AZRHCOAXTMKTDJ-CQSZACIVSA-N 0.000 description 1
- AISXBZVAYNUAKB-UHFFFAOYSA-N 1,1,4,4,6-pentamethyl-2,3-dihydronaphthalene Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C)=CC=2 AISXBZVAYNUAKB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FEHJPFOMBHXEPY-CQSZACIVSA-N 1-[(6r)-6-ethyl-3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl]ethanone Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)[C@H](CC)CC(C)(C)C2=C1 FEHJPFOMBHXEPY-CQSZACIVSA-N 0.000 description 1
- FEHJPFOMBHXEPY-AWEZNQCLSA-N 1-[(6s)-6-ethyl-3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl]ethanone Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)[C@@H](CC)CC(C)(C)C2=C1 FEHJPFOMBHXEPY-AWEZNQCLSA-N 0.000 description 1
- LQXGUMYMOOXEIL-UHFFFAOYSA-N 2-(1,1,4,4,7-pentamethyl-2,3-dihydronaphthalen-2-yl)acetic acid Chemical compound CC1(C)C(CC(O)=O)CC(C)(C)C=2C1=CC(C)=CC=2 LQXGUMYMOOXEIL-UHFFFAOYSA-N 0.000 description 1
- LQXGUMYMOOXEIL-LBPRGKRZSA-N 2-[(2r)-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalen-2-yl]acetic acid Chemical compound C([C@H](CC(O)=O)C1(C)C)C(C)(C)C=2C1=CC(C)=CC=2 LQXGUMYMOOXEIL-LBPRGKRZSA-N 0.000 description 1
- LQXGUMYMOOXEIL-GFCCVEGCSA-N 2-[(2s)-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalen-2-yl]acetic acid Chemical compound C([C@@H](CC(O)=O)C1(C)C)C(C)(C)C=2C1=CC(C)=CC=2 LQXGUMYMOOXEIL-GFCCVEGCSA-N 0.000 description 1
- ZEUZBDYJXCWXAT-CYBMUJFWSA-N 2-[(2s)-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalen-2-yl]ethanol Chemical compound C([C@@H](CCO)C1(C)C)C(C)(C)C=2C1=CC(C)=CC=2 ZEUZBDYJXCWXAT-CYBMUJFWSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12722481A JPS5829721A (ja) | 1981-08-12 | 1981-08-12 | テトラヒドロナフタレン誘導体の製造方法 |
| DE8282105071T DE3266350D1 (en) | 1981-06-11 | 1982-06-09 | Tetrahydronaphthalene derivatives and their production |
| EP82105071A EP0071006B1 (en) | 1981-06-11 | 1982-06-09 | Tetrahydronaphthalene derivatives and their production |
| US06/902,063 US4767882A (en) | 1981-06-11 | 1986-08-26 | Tetrahydronaphthalene derivatives and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12722481A JPS5829721A (ja) | 1981-08-12 | 1981-08-12 | テトラヒドロナフタレン誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5829721A JPS5829721A (ja) | 1983-02-22 |
| JPS6316365B2 true JPS6316365B2 (zh) | 1988-04-08 |
Family
ID=14954795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12722481A Granted JPS5829721A (ja) | 1981-06-11 | 1981-08-12 | テトラヒドロナフタレン誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829721A (zh) |
-
1981
- 1981-08-12 JP JP12722481A patent/JPS5829721A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5829721A (ja) | 1983-02-22 |
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