JPH0355459B2 - - Google Patents
Info
- Publication number
- JPH0355459B2 JPH0355459B2 JP14860982A JP14860982A JPH0355459B2 JP H0355459 B2 JPH0355459 B2 JP H0355459B2 JP 14860982 A JP14860982 A JP 14860982A JP 14860982 A JP14860982 A JP 14860982A JP H0355459 B2 JPH0355459 B2 JP H0355459B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclopentenone
- hydroxy
- methyl
- group
- reaction
- 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
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 12
- -1 cyanohexyl group Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 4
- 238000000605 extraction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FKMJJDZYBRVQBZ-SNAWJCMRSA-N 4-hydroxy-5-[(e)-pent-1-enyl]cyclopent-2-en-1-one Chemical compound CCC\C=C\C1C(O)C=CC1=O FKMJJDZYBRVQBZ-SNAWJCMRSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- HCGSXRYUKLYOFD-UHFFFAOYSA-N (2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl) acetate Chemical compound CCCCCC1=C(C)C(OC(C)=O)CC1=O HCGSXRYUKLYOFD-UHFFFAOYSA-N 0.000 description 1
- MDFPPPIHFJPKRF-UHFFFAOYSA-N (2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl) acetate Chemical compound CC(=O)OC1CC(=O)C(CC=C)=C1C MDFPPPIHFJPKRF-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KUZRPQHDPJDXAZ-UHFFFAOYSA-N 4-hydroxy-4,5-dimethylcyclopent-2-en-1-one Chemical compound CC1C(=O)C=CC1(C)O KUZRPQHDPJDXAZ-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
- QSBOWRGBKFLEFP-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-pentylcyclopent-2-en-1-one Chemical compound CCCCCC1C(=O)C=CC1(C)O QSBOWRGBKFLEFP-UHFFFAOYSA-N 0.000 description 1
- BZTCJPVCZOODFD-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-phenylcyclopent-2-en-1-one Chemical compound CC1(O)C=CC(=O)C1C1=CC=CC=C1 BZTCJPVCZOODFD-UHFFFAOYSA-N 0.000 description 1
- BLXRCUAXNAVKIQ-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-prop-2-ynylcyclopent-2-en-1-one Chemical compound CC1(O)C=CC(=O)C1CC#C BLXRCUAXNAVKIQ-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
- YBOSXQPPIAJHBR-UHFFFAOYSA-N 4-hydroxy-5-methylcyclopent-2-en-1-one Chemical compound CC1C(O)C=CC1=O YBOSXQPPIAJHBR-UHFFFAOYSA-N 0.000 description 1
- GBJLMAFSBULEHH-UHFFFAOYSA-N 4-hydroxy-5-pent-2-ynylcyclopent-2-en-1-one Chemical compound CCC#CCC1C(O)C=CC1=O GBJLMAFSBULEHH-UHFFFAOYSA-N 0.000 description 1
- PJVOCKSLNHMZQP-UHFFFAOYSA-N 4-hydroxy-5-pentylcyclopent-2-en-1-one Chemical compound CCCCCC1C(O)C=CC1=O PJVOCKSLNHMZQP-UHFFFAOYSA-N 0.000 description 1
- XTMOUGOROVDTGR-UHFFFAOYSA-N 4-hydroxy-5-phenylcyclopent-2-en-1-one Chemical compound OC1C=CC(=O)C1C1=CC=CC=C1 XTMOUGOROVDTGR-UHFFFAOYSA-N 0.000 description 1
- ONQGUUWSGZTDPO-UHFFFAOYSA-N 4-hydroxy-5-prop-2-enylcyclopent-2-en-1-one Chemical compound OC1C=CC(=O)C1CC=C ONQGUUWSGZTDPO-UHFFFAOYSA-N 0.000 description 1
- BFSFRKPXQRZGQB-UHFFFAOYSA-N 4-hydroxy-5-prop-2-ynylcyclopent-2-en-1-one Chemical compound OC1C=CC(=O)C1CC#C BFSFRKPXQRZGQB-UHFFFAOYSA-N 0.000 description 1
- DHZISXYGHCFXSZ-UHFFFAOYSA-N 4-hydroxy-5-propan-2-ylcyclopent-2-en-1-one Chemical compound CC(C)C1C(O)C=CC1=O DHZISXYGHCFXSZ-UHFFFAOYSA-N 0.000 description 1
- NDLFPIAPKCLHDQ-UHFFFAOYSA-N 4-hydroxy-5-propylcyclopent-2-en-1-one Chemical compound CCCC1C(O)C=CC1=O NDLFPIAPKCLHDQ-UHFFFAOYSA-N 0.000 description 1
- QWWTUUWNBYWOPE-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-hydroxy-4-methylcyclopent-2-en-1-one Chemical compound CC1(O)C=CC(=O)C1C1=CC=C(Cl)C=C1 QWWTUUWNBYWOPE-UHFFFAOYSA-N 0.000 description 1
- VSAISQPJOKIOJC-UHFFFAOYSA-N 5-butyl-4-hydroxy-4-methylcyclopent-2-en-1-one Chemical compound CCCCC1C(=O)C=CC1(C)O VSAISQPJOKIOJC-UHFFFAOYSA-N 0.000 description 1
- LNGQOESWVQUPGX-UHFFFAOYSA-N 5-butyl-4-hydroxycyclopent-2-en-1-one Chemical compound CCCCC1C(O)C=CC1=O LNGQOESWVQUPGX-UHFFFAOYSA-N 0.000 description 1
- VGTUXRVDBMHWBD-UHFFFAOYSA-N 5-ethyl-4-hydroxy-4-methylcyclopent-2-en-1-one Chemical compound CCC1C(=O)C=CC1(C)O VGTUXRVDBMHWBD-UHFFFAOYSA-N 0.000 description 1
- YBYBHQDUFSBDDA-UHFFFAOYSA-N 5-ethyl-4-hydroxycyclopent-2-en-1-one Chemical compound CCC1C(O)C=CC1=O YBYBHQDUFSBDDA-UHFFFAOYSA-N 0.000 description 1
- YVJWEFBXOALURR-UHFFFAOYSA-N 5-heptyl-4-hydroxy-4-methylcyclopent-2-en-1-one Chemical compound CCCCCCCC1C(=O)C=CC1(C)O YVJWEFBXOALURR-UHFFFAOYSA-N 0.000 description 1
- JOJDSFWDKMJLIB-UHFFFAOYSA-N 5-heptyl-4-hydroxycyclopent-2-en-1-one Chemical compound CCCCCCCC1C(O)C=CC1=O JOJDSFWDKMJLIB-UHFFFAOYSA-N 0.000 description 1
- CHKGQHDUAIYQOY-UHFFFAOYSA-N 5-hexyl-4-hydroxy-4-methylcyclopent-2-en-1-one Chemical compound CCCCCCC1C(=O)C=CC1(C)O CHKGQHDUAIYQOY-UHFFFAOYSA-N 0.000 description 1
- HGSCAIODYYGEOB-UHFFFAOYSA-N 5-hexyl-4-hydroxycyclopent-2-en-1-one Chemical compound CCCCCCC1C(O)C=CC1=O HGSCAIODYYGEOB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FKMJJDZYBRVQBZ-UHFFFAOYSA-N OC1C(C(C=C1)=O)C=C/CCC Chemical compound OC1C(C(C=C1)=O)C=C/CCC FKMJJDZYBRVQBZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- GTUVXOOHBUUGBH-UHFFFAOYSA-N furan;methanol Chemical class OC.C=1C=COC=1 GTUVXOOHBUUGBH-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14860982A JPS5939852A (ja) | 1982-08-26 | 1982-08-26 | シクロペンテノンエステルの製造方法 |
| US06/523,602 US4535182A (en) | 1982-08-26 | 1983-08-16 | Process for preparing 2-cyclopentenone esters |
| EP83108390A EP0102066B1 (en) | 1982-08-26 | 1983-08-25 | Process for preparing 2-cyclopentenone esters |
| DE8383108390T DE3361426D1 (en) | 1982-08-26 | 1983-08-25 | Process for preparing 2-cyclopentenone esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14860982A JPS5939852A (ja) | 1982-08-26 | 1982-08-26 | シクロペンテノンエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5939852A JPS5939852A (ja) | 1984-03-05 |
| JPH0355459B2 true JPH0355459B2 (enrdf_load_stackoverflow) | 1991-08-23 |
Family
ID=15456599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14860982A Granted JPS5939852A (ja) | 1982-08-26 | 1982-08-26 | シクロペンテノンエステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5939852A (enrdf_load_stackoverflow) |
-
1982
- 1982-08-26 JP JP14860982A patent/JPS5939852A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5939852A (ja) | 1984-03-05 |