JPH0446935B2 - - Google Patents
Info
- Publication number
- JPH0446935B2 JPH0446935B2 JP62307416A JP30741687A JPH0446935B2 JP H0446935 B2 JPH0446935 B2 JP H0446935B2 JP 62307416 A JP62307416 A JP 62307416A JP 30741687 A JP30741687 A JP 30741687A JP H0446935 B2 JPH0446935 B2 JP H0446935B2
- Authority
- JP
- Japan
- Prior art keywords
- methyllithium
- reaction
- ether
- copper
- alkanols
- 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
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- -1 copper halide Chemical class 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 6
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GYSCXPVAKHVAAY-VIFPVBQESA-N (3s)-nonan-3-ol Chemical compound CCCCCC[C@@H](O)CC GYSCXPVAKHVAAY-VIFPVBQESA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- NJWSNNWLBMSXQR-MRVPVSSYSA-N (2r)-2-hexyloxirane Chemical compound CCCCCC[C@@H]1CO1 NJWSNNWLBMSXQR-MRVPVSSYSA-N 0.000 description 2
- FRCQVIXJQKSHHF-UHFFFAOYSA-N 1-(morpholin-4-ylmethyl)cyclohexan-1-amine Chemical compound C1COCCN1CC1(N)CCCCC1 FRCQVIXJQKSHHF-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- IOHJQSFEAYDZGF-UHFFFAOYSA-N 2-dodecyloxirane Chemical compound CCCCCCCCCCCCC1CO1 IOHJQSFEAYDZGF-UHFFFAOYSA-N 0.000 description 1
- CEUXMUYHMURJFZ-UHFFFAOYSA-N 2-heptadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCC1CO1 CEUXMUYHMURJFZ-UHFFFAOYSA-N 0.000 description 1
- GXOYTMXAKFMIRK-UHFFFAOYSA-N 2-heptyloxirane Chemical compound CCCCCCCC1CO1 GXOYTMXAKFMIRK-UHFFFAOYSA-N 0.000 description 1
- QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- LXVAZSIZYQIZCR-UHFFFAOYSA-N 2-nonyloxirane Chemical compound CCCCCCCCCC1CO1 LXVAZSIZYQIZCR-UHFFFAOYSA-N 0.000 description 1
- BHZBVWCLMYQFQX-UHFFFAOYSA-N 2-octadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCCC1CO1 BHZBVWCLMYQFQX-UHFFFAOYSA-N 0.000 description 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
- XSNXNMMWBCZUSS-UHFFFAOYSA-N 2-pentadecyloxirane Chemical compound CCCCCCCCCCCCCCCC1CO1 XSNXNMMWBCZUSS-UHFFFAOYSA-N 0.000 description 1
- NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical compound CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- QMIBIXKZPBEGTE-UHFFFAOYSA-N 2-tridecyloxirane Chemical compound CCCCCCCCCCCCCC1CO1 QMIBIXKZPBEGTE-UHFFFAOYSA-N 0.000 description 1
- ZKAPVLMBPUYKKP-UHFFFAOYSA-N 2-undecyloxirane Chemical compound CCCCCCCCCCCC1CO1 ZKAPVLMBPUYKKP-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- HCARCYFXWDRVBZ-UHFFFAOYSA-N undecan-3-ol Chemical compound CCCCCCCCC(O)CC HCARCYFXWDRVBZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62307416A JPH01149741A (ja) | 1987-12-07 | 1987-12-07 | ３−アルカノール類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62307416A JPH01149741A (ja) | 1987-12-07 | 1987-12-07 | ３−アルカノール類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01149741A JPH01149741A (ja) | 1989-06-12 |
| JPH0446935B2 true JPH0446935B2 (US07223432-20070529-C00017.png) | 1992-07-31 |
Family
ID=17968793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62307416A Granted JPH01149741A (ja) | 1987-12-07 | 1987-12-07 | ３−アルカノール類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01149741A (US07223432-20070529-C00017.png) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51101909A (US07223432-20070529-C00017.png) * | 1975-02-03 | 1976-09-08 | Anic Spa | |
| JPS5473710A (en) * | 1977-11-17 | 1979-06-13 | Asahi Chem Ind Co Ltd | Production of 2-butene-1,4-diol derivative |
-
1987
- 1987-12-07 JP JP62307416A patent/JPH01149741A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51101909A (US07223432-20070529-C00017.png) * | 1975-02-03 | 1976-09-08 | Anic Spa | |
| JPS5473710A (en) * | 1977-11-17 | 1979-06-13 | Asahi Chem Ind Co Ltd | Production of 2-butene-1,4-diol derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01149741A (ja) | 1989-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20040024254A1 (en) | Process for preparation of optically active halogeno hydroxypropyl compound and glycidyl compound | |
| US20100267988A1 (en) | Processes for preparing intermediate compounds useful for the preparation of cinacalcet | |
| JPS6176479A (ja) | ４，４‐ジ置換５‐メチレン‐１，３‐ジオキソラン‐２‐オンの製法 | |
| US4822925A (en) | Organosalts of metalate anions and process for the production of alkylene glycols therewith | |
| JPH0446935B2 (US07223432-20070529-C00017.png) | ||
| JP2528972B2 (ja) | アルキニル化合物の連続製造方法 | |
| JPH0456016B2 (US07223432-20070529-C00017.png) | ||
| JP2582288B2 (ja) | 光学活性な１―フルオロ―２―アルカノール類及びその製造方法 | |
| EP0160328A1 (en) | Organosalts of metalate anions and process for the production of alkylene glycols therewith | |
| JPS624255A (ja) | エチレンシアンヒドリン及びそのエ−テルの共同製法 | |
| JP2649572B2 (ja) | 光学活性な２―フルオロ―２―メチル―１―アルカノール類及びその製造方法 | |
| JP2582289B2 (ja) | 光学活性を有する２―フルオロ―１―アルカノール類の製造方法 | |
| KR0126769B1 (ko) | (아릴)-(디메틸)-(3-(4-플루오로-3-아릴옥시페닐)프로필)실란의 제조방법 | |
| Caccia et al. | Synthesis of (+)-(S)-4-s. Butyl and (+)-(S)-2-Methyl-4-s. Butylpyridine | |
| US6207847B1 (en) | Manufacture of optically active halohydrin trialkylsilyl ethers | |
| JP3505766B2 (ja) | 光学活性α−ヒドロキシケトン誘導体の製造方法 | |
| JPH08217775A (ja) | 新規クラウンチオエーテル及びその遷移金属錯体並びにこれを用いる光学活性アルコールの製造方法 | |
| US4812566A (en) | Process for preparing 1-dodecylazacycloheptane-2-one | |
| JP2692247B2 (ja) | 光学活性１，３‐ジオールの製造方法 | |
| JPH0546345B2 (US07223432-20070529-C00017.png) | ||
| JPH01100138A (ja) | 光学活性を有する２‐アルキル‐１‐アルカノール類の製造方法 | |
| JPS61126048A (ja) | 光学活性４−ヒドロキシ−２−シクロペンテノン類の製法 | |
| JPS5827775B2 (ja) | 反応を促進する方法 | |
| JPH0420417B2 (US07223432-20070529-C00017.png) | ||
| JPH0360832B2 (US07223432-20070529-C00017.png) |
