JPS6159632B2 - - Google Patents
Info
- Publication number
- JPS6159632B2 JPS6159632B2 JP9331381A JP9331381A JPS6159632B2 JP S6159632 B2 JPS6159632 B2 JP S6159632B2 JP 9331381 A JP9331381 A JP 9331381A JP 9331381 A JP9331381 A JP 9331381A JP S6159632 B2 JPS6159632 B2 JP S6159632B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- optically active
- reaction
- acid
- compound
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 description 2
- 241000723353 Chrysanthemum Species 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-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
- 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
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-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
- IEBXZRQOXHLIGF-UHFFFAOYSA-N 5,5-dimethyl-4-(2-methylprop-1-enyl)oxolan-2-one Chemical compound CC(C)=CC1CC(=O)OC1(C)C IEBXZRQOXHLIGF-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- -1 malonic acid ester Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9331381A JPS57209282A (en) | 1981-06-16 | 1981-06-16 | Lactone derivative and its preparation |
| EP82105071A EP0071006B1 (en) | 1981-06-11 | 1982-06-09 | Tetrahydronaphthalene derivatives and their production |
| DE8282105071T DE3266350D1 (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 |
|---|---|---|---|
| JP9331381A JPS57209282A (en) | 1981-06-16 | 1981-06-16 | Lactone derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57209282A JPS57209282A (en) | 1982-12-22 |
| JPS6159632B2 true JPS6159632B2 (ru) | 1986-12-17 |
Family
ID=14078820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9331381A Granted JPS57209282A (en) | 1981-06-11 | 1981-06-16 | Lactone derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57209282A (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04131621U (ja) * | 1991-05-24 | 1992-12-03 | 隆之 井田 | ヘルメツト |
-
1981
- 1981-06-16 JP JP9331381A patent/JPS57209282A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04131621U (ja) * | 1991-05-24 | 1992-12-03 | 隆之 井田 | ヘルメツト |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57209282A (en) | 1982-12-22 |
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