JPH0420416B2 - - Google Patents

Info

Publication number: JPH0420416B2
Authority: JP; Japan
Prior art keywords: tetrahydrofuran; reaction; optically active; halogeno; octanol
Prior art date: 1987-06-19
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

Application number

JP22292787A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6470423A (en

Inventor

Junko Umezawa

Keizo Furuhashi

Original Assignee

Nippon Mining Co

Priority date (The priority date 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 date listed.)

1987-06-19

Filing date

1987-09-08

Publication date

1992-04-02

1987-09-08 Application filed by Nippon Mining Co filed Critical Nippon Mining Co

1987-09-08 Priority to JP22292787A priority Critical patent/JPS6470423A/ja

1989-03-15 Publication of JPS6470423A publication Critical patent/JPS6470423A/ja

1992-04-02 Publication of JPH0420416B2 publication Critical patent/JPH0420416B2/ja

Status Granted legal-status Critical Current

Links

230000003287 optical effect Effects 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000000034 method Methods 0.000 description 9
229910021589 Copper(I) bromide Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 8
229910021591 Copper(I) chloride Inorganic materials 0.000 description 7
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 5
NJWSNNWLBMSXQR-MRVPVSSYSA-N (2r)-2-hexyloxirane Chemical compound CCCCCC[C@@H]1CO1 NJWSNNWLBMSXQR-MRVPVSSYSA-N 0.000 description 4
XUJYYGPRWZWHLT-UHFFFAOYSA-N 1-chlorooctan-2-ol Chemical compound CCCCCCC(O)CCl XUJYYGPRWZWHLT-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000008363 phosphate buffer Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
UOOOQHMFMRVNJN-UHFFFAOYSA-N 1-bromooctan-2-ol Chemical compound CCCCCCC(O)CBr UOOOQHMFMRVNJN-UHFFFAOYSA-N 0.000 description 2
VWVAGHKETJVBII-UHFFFAOYSA-N 2-chlorooctan-1-ol Chemical compound CCCCCCC(Cl)CO VWVAGHKETJVBII-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
IOHJQSFEAYDZGF-CQSZACIVSA-N (2r)-2-dodecyloxirane Chemical compound CCCCCCCCCCCC[C@@H]1CO1 IOHJQSFEAYDZGF-CQSZACIVSA-N 0.000 description 1
AAMHBRRZYSORSH-SNVBAGLBSA-N (2r)-2-octyloxirane Chemical compound CCCCCCCC[C@@H]1CO1 AAMHBRRZYSORSH-SNVBAGLBSA-N 0.000 description 1
JJYKJUXBWFATTE-SECBINFHSA-N (2r)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid Chemical compound CO[C@](C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-SECBINFHSA-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
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
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
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
SJIWUNNSRFWATG-UHFFFAOYSA-N 4-[2-(2-hydroxyethoxy)ethoxy]-4-oxobutanoic acid Chemical compound OCCOCCOC(=O)CCC(O)=O SJIWUNNSRFWATG-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 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
239000013543 active substance Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000005445 natural material Substances 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP22292787A 1987-06-19 1987-09-08 Production of 1-halogeno-2-alkalols having optical activity Granted JPS6470423A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP22292787A JPS6470423A (en)	1987-06-19	1987-09-08	Production of 1-halogeno-2-alkalols having optical activity

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP15127087		1987-06-19
JP22292787A JPS6470423A (en)	1987-06-19	1987-09-08	Production of 1-halogeno-2-alkalols having optical activity

Publications (2)

Publication Number	Publication Date
JPS6470423A JPS6470423A (en)	1989-03-15
JPH0420416B2 true JPH0420416B2 (2)	1992-04-02

Family

ID=26480571

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP22292787A Granted JPS6470423A (en)	1987-06-19	1987-09-08	Production of 1-halogeno-2-alkalols having optical activity

Country Status (1)

Country	Link
JP (1)	JPS6470423A (2)

1987
- 1987-09-08 JP JP22292787A patent/JPS6470423A/ja active Granted

Also Published As

Publication number	Publication date
JPS6470423A (en)	1989-03-15

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