JPH043373B2 - - Google Patents

Info

Publication number: JPH043373B2
Authority: JP; Japan
Prior art keywords: group; hydrogen atom; general formula; formula; atom
Prior art date: 1983-11-14
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

JP21457283A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60105640A (ja

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.)

1983-11-14

Filing date

1983-11-14

Publication date

1992-01-23

1983-11-14 Application filed filed Critical

1983-11-14 Priority to JP21457283A priority Critical patent/JPS60105640A/ja

1984-11-14 Priority to KR1019840007119A priority patent/KR850004087A/ko

1985-06-11 Publication of JPS60105640A publication Critical patent/JPS60105640A/ja

1992-01-23 Publication of JPH043373B2 publication Critical patent/JPH043373B2/ja

Status Granted legal-status Critical Current

Links

125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
-1 methylenedioxy group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000000243 solution Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
230000000397 acetylating effect Effects 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
UJSJQZQQPHGLJG-UHFFFAOYSA-N pent-2-yn-1-ol Chemical compound CCC#C[CH]O UJSJQZQQPHGLJG-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
BTCIFTQVULXRDT-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-2-methylpropanal Chemical compound CCOC1=CC=C(C(C)(C)C=O)C=C1 BTCIFTQVULXRDT-UHFFFAOYSA-N 0.000 description 1
MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000012827 research and development Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

JP21457283A 1983-11-14 1983-11-14 フェニルカルビノ−ル誘導体 Granted JPS60105640A (ja)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
JP21457283A JPS60105640A (ja)	1983-11-14	1983-11-14	フェニルカルビノ−ル誘導体
KR1019840007119A KR850004087A (ko)	1983-11-14	1984-11-14	탄화 수소계 화합물의 제조방법

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP21457283A JPS60105640A (ja)	1983-11-14	1983-11-14	フェニルカルビノ−ル誘導体

Publications (2)

Publication Number	Publication Date
JPS60105640A JPS60105640A (ja)	1985-06-11
JPH043373B2 true JPH043373B2 (de)	1992-01-23

Family

ID=16657932

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP21457283A Granted JPS60105640A (ja)	1983-11-14	1983-11-14	フェニルカルビノ−ル誘導体

Country Status (1)

Country	Link
JP (1)	JPS60105640A (de)

1983
- 1983-11-14 JP JP21457283A patent/JPS60105640A/ja active Granted

Also Published As

Publication number	Publication date
JPS60105640A (ja)	1985-06-11

Publication	Publication Date	Title
JPH0729997B2 (ja)	1995-04-05	フェニルアルコキシ誘導体
JPH043373B2 (de)	1992-01-23
JPH043374B2 (de)	1992-01-23
JPH043371B2 (de)	1992-01-23
US5254708A (en)	1993-10-19	Substituted cyclic ketones, substituted cyclic enones, and process for producing the same
JPS6111210B2 (de)	1986-04-01
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JP3660023B2 (ja)	2005-06-15	ビスインデニル誘導体
EP0170517B1 (de)	1989-12-27	Verfahren zur Herstellung von 1,2-Aminoalkoholen
US5288928A (en)	1994-02-22	Asymmetrical hydrogenation
US4524221A (en)	1985-06-18	Process for the production of acyloins
US4556723A (en)	1985-12-03	Process for the production of acyloins
JPH04270294A (ja)	1992-09-25	α−メチレンシクロペンタノン誘導体の製造法
US5227505A (en)	1993-07-13	Substituted cyclic ketones, substituted cyclic enones, and process for producing the same
US5231208A (en)	1993-07-27	Substituted cyclic ketones, substituted cyclic enones, and process for producing the same
JP3590980B2 (ja)	2004-11-17	光学活性３級ホスフィン化合物、それを配位子とする遷移金属錯体およびその用途
US4377532A (en)	1983-03-22	3-Phenoxybenzyl compounds
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JP4243397B2 (ja)	2009-03-25	新規な不飽和２級アルコールおよびその製造法
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JP4505876B2 (ja)	2010-07-21	４−ハロベンゾフラン誘導体及びその製造方法
JPH0112757B2 (de)	1989-03-02
WO1997045433A1 (en)	1997-12-04	Process for the preparation of benzyl-metal compounds and process for the preparation of 4-phenyl-1-butenes by the use of the same
KR20090087732A (ko)	2009-08-18	1-(2-하이드록시페닐)부타-2-엔-1-온 또는 크로멘-4-온유도체의 제조방법
JP2005162637A (ja)	2005-06-23	ホスフィン化合物および製造方法