JPH0570630B2 - - Google Patents
Info
- Publication number
- JPH0570630B2 JPH0570630B2 JP59026647A JP2664784A JPH0570630B2 JP H0570630 B2 JPH0570630 B2 JP H0570630B2 JP 59026647 A JP59026647 A JP 59026647A JP 2664784 A JP2664784 A JP 2664784A JP H0570630 B2 JPH0570630 B2 JP H0570630B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- hydroxy
- cyclopentenone
- cyclopentenyloxy
- oxa
- 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 - Lifetime
Links
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 15
- DHNDDRBMUVFQIZ-UHFFFAOYSA-N 4-hydroxycyclopent-2-en-1-one Chemical compound OC1CC(=O)C=C1 DHNDDRBMUVFQIZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000002596 lactones Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- QHAPONCMFJQXEN-OVEKKEMJSA-N (1r,5s)-4-hydroxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one Chemical compound O=C1OC(O)[C@H]2[C@@H]1C2(C)C QHAPONCMFJQXEN-OVEKKEMJSA-N 0.000 claims description 5
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HFCMQKFXCMZZMZ-UHFFFAOYSA-N bicyclo[3.1.0]hexan-2-one Chemical compound O=C1CCC2CC12 HFCMQKFXCMZZMZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- -1 Cyclopentenone ethers Chemical class 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2664784A JPS60169474A (ja) | 1984-02-14 | 1984-02-14 | シクロペンテノンエ−テル類の製造方法 |
| DE8585101494T DE3560714D1 (en) | 1984-02-14 | 1985-02-12 | Process for preparing optically active 4-hydroxy-2-cyclipentenones |
| US06/700,890 US4714782A (en) | 1984-02-14 | 1985-02-12 | Process for preparing optically active 4-hydroxy-2-cyclopentenones |
| EP85101494A EP0153653B1 (en) | 1984-02-14 | 1985-02-12 | Process for preparing optically active 4-hydroxy-2-cyclipentenones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2664784A JPS60169474A (ja) | 1984-02-14 | 1984-02-14 | シクロペンテノンエ−テル類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60169474A JPS60169474A (ja) | 1985-09-02 |
| JPH0570630B2 true JPH0570630B2 (hu) | 1993-10-05 |
Family
ID=12199234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2664784A Granted JPS60169474A (ja) | 1984-02-14 | 1984-02-14 | シクロペンテノンエ−テル類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60169474A (hu) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57159777A (en) * | 1981-03-27 | 1982-10-01 | Teijin Ltd | 4-hydroxycyclopentenone compound and its preparation |
-
1984
- 1984-02-14 JP JP2664784A patent/JPS60169474A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57159777A (en) * | 1981-03-27 | 1982-10-01 | Teijin Ltd | 4-hydroxycyclopentenone compound and its preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60169474A (ja) | 1985-09-02 |
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