SK6952001A3 - Processes for the preparation of (p-chlorophenyl)propanol derivatives - Google Patents

Processes for the preparation of (p-chlorophenyl)propanol derivatives Download PDF

Info

Publication number: SK6952001A3
Authority: SK; Slovakia
Prior art keywords: compound; preparation; reaction; chlorophenyl; mol
Prior art date: 1998-12-11

Application number

SK695-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Hiroo Matsumoto

Minako Kamikawaji

Takashi Horiuchi

Original Assignee

Nissan Chemical Ind Ltd

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.)

1998-12-11

Filing date

1999-11-29

Publication date

2001-12-03

1999-11-29 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2001-12-03 Publication of SK6952001A3 publication Critical patent/SK6952001A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 11
TXAWBKBMGZKBNN-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-1-ol Chemical class CCC(O)C1=CC=C(Cl)C=C1 TXAWBKBMGZKBNN-UHFFFAOYSA-N 0.000 title description 3
GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 claims abstract description 6
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims abstract description 6
238000007259 addition reaction Methods 0.000 claims description 10
229940125782 compound 2 Drugs 0.000 claims description 6
229940125904 compound 1 Drugs 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
150000004808 allyl alcohols Chemical class 0.000 claims 1
-1 alcohol compound Chemical class 0.000 abstract description 10
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract description 10
150000001875 compounds Chemical class 0.000 abstract description 10
230000008878 coupling Effects 0.000 abstract 1
238000010168 coupling process Methods 0.000 abstract 1
238000005859 coupling reaction Methods 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
238000005893 bromination reaction Methods 0.000 description 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
150000003242 quaternary ammonium salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
ZHBIWFGGIKFSHZ-UHFFFAOYSA-N 3-(4-chlorophenyl)propan-1-ol Chemical compound OCCCC1=CC=C(Cl)C=C1 ZHBIWFGGIKFSHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
MPEOPBCQHNWNFB-UHFFFAOYSA-N 1-chloro-2-iodobenzene Chemical compound ClC1=CC=CC=C1I MPEOPBCQHNWNFB-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000006298 dechlorination reaction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
UBOFXBQTRQSKMY-UHFFFAOYSA-N 1-(2-chlorophenyl)propan-1-ol Chemical class CCC(O)C1=CC=CC=C1Cl UBOFXBQTRQSKMY-UHFFFAOYSA-N 0.000 description 1
AKMIGKNTCCSJNQ-UHFFFAOYSA-N 1-(3-bromopropyl)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1CCCBr AKMIGKNTCCSJNQ-UHFFFAOYSA-N 0.000 description 1
WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
RROVHEOLZYPASG-UHFFFAOYSA-N 3-(2-chlorophenyl)propan-1-ol Chemical compound OCCCC1=CC=CC=C1Cl RROVHEOLZYPASG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical group 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

SK695-2001A 1998-12-11 1999-11-29 Processes for the preparation of (p-chlorophenyl)propanol derivatives SK6952001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP35252998		1998-12-11
PCT/JP1999/006654 WO2000035843A1 (fr)	1998-12-11	1999-11-29	PROCEDE DE PREPARATION DE DERIVES DE (p-CHLOROPHENYL) PROPANOL

Publications (1)

Publication Number	Publication Date
SK6952001A3 true SK6952001A3 (en)	2001-12-03

Family

ID=18424696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK695-2001A SK6952001A3 (en)	1998-12-11	1999-11-29	Processes for the preparation of (p-chlorophenyl)propanol derivatives

Country Status (16)

Country	Link
US (1)	US6407298B1 (cs)
EP (1)	EP1138660A4 (cs)
JP (1)	JP4474773B2 (cs)
KR (1)	KR20010086010A (cs)
CN (1)	CN1329586A (cs)
AU (1)	AU755010B2 (cs)
CA (1)	CA2347813A1 (cs)
CZ (1)	CZ20011368A3 (cs)
IL (1)	IL143665A0 (cs)
NO (1)	NO20012811L (cs)
NZ (1)	NZ511022A (cs)
SK (1)	SK6952001A3 (cs)
TW (1)	TW538027B (cs)
UA (1)	UA52841C2 (cs)
WO (1)	WO2000035843A1 (cs)
ZA (1)	ZA200103328B (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7935173B1 (en)	2010-07-23	2011-05-03	Metals Recovery Technology Inc.	Process for recovery of precious metals
CN102757318B (zh) *	2011-04-29	2015-06-24	上海医药工业研究院	一种阿利克伦中间体的制备方法
JP2023128936A (ja) *	2022-03-04	2023-09-14	キオクシア株式会社	情報処理装置及び初期辞書作成方法
CN114716296B (zh) *	2022-03-25	2023-12-12	润药仁智(北京)科技有限公司	一种烷基卤化物的高效卤化合成方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE299187C (cs)
US2184526A (en) *	1937-05-27	1939-12-26	Du Pont	Perfume compositions and process of making the same
DE1132914B (de) *	1957-05-09	1962-07-12	Siegfried Ag	Verfahren zur Herstellung von Carbaminsaeureestern von Aralkyl-alkoholen
US3487116A (en) *	1966-06-16	1969-12-30	Engelhard Ind Inc	Method for hydrogenation of cinnamyl alcohols
US3663626A (en) *	1969-05-01	1972-05-16	Universal Oil Prod Co	Hydrogenation of arylaldehydes
SE7407449L (cs) *	1973-07-20	1975-01-21	Ciba Geigy Ag
US4070374A (en) *	1975-06-16	1978-01-24	Givaudan Corporation	Process for the preparation of aryl substituted aldehydes, ketones and alcohols
JPS5581831A (en) *	1978-12-15	1980-06-20	Toray Ind Inc	Preparation of propionaldehyde derivative
CA1211754A (en) *	1980-07-09	1986-09-23	David Webb	Process for the production of phenyl substituted alcohols
JPS59163336A (ja) *	1983-03-09	1984-09-14	Nippon Petrochem Co Ltd	アルデヒドの製造法
FR2623798B1 (fr) *	1987-11-26	1990-05-04	Lucien Laboratoires	Derives de trifluoromethyl-1 tetralines, leur preparation et leur application pour la synthese de composes presentant des proprietes therapeutiques
DD299186A5 (de) *	1990-10-01	1992-04-02	E.R. Squibb U. Sons,Inc.,Us	Phenylen-7-oxabicycloheptyl-substituierte heterocycloamid-prostaglandinanaloga
UA59384C2 (uk) *	1996-12-20	2003-09-15	Пфайзер, Інк.	Похідні сульфонамідів та амідів як агоністи простагландину, фармацевтична композиція та способи лікування на їх основі

1999
- 1999-11-29 KR KR1020017005793A patent/KR20010086010A/ko not_active Ceased
- 1999-11-29 US US09/830,555 patent/US6407298B1/en not_active Expired - Fee Related
- 1999-11-29 SK SK695-2001A patent/SK6952001A3/sk unknown
- 1999-11-29 WO PCT/JP1999/006654 patent/WO2000035843A1/ja not_active Ceased
- 1999-11-29 UA UA2001053136A patent/UA52841C2/uk unknown
- 1999-11-29 NZ NZ511022A patent/NZ511022A/en unknown
- 1999-11-29 IL IL14366599A patent/IL143665A0/xx unknown
- 1999-11-29 CN CN99814048A patent/CN1329586A/zh active Pending
- 1999-11-29 CZ CZ20011368A patent/CZ20011368A3/cs unknown
- 1999-11-29 EP EP99973408A patent/EP1138660A4/en not_active Withdrawn
- 1999-11-29 AU AU14114/00A patent/AU755010B2/en not_active Ceased
- 1999-11-29 CA CA002347813A patent/CA2347813A1/en not_active Abandoned
- 1999-11-29 JP JP2000588107A patent/JP4474773B2/ja not_active Expired - Lifetime
- 1999-12-03 TW TW088121220A patent/TW538027B/zh active
2001
- 2001-04-24 ZA ZA200103328A patent/ZA200103328B/en unknown
- 2001-06-07 NO NO20012811A patent/NO20012811L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO20012811D0 (no)	2001-06-07
JP4474773B2 (ja)	2010-06-09
UA52841C2 (uk)	2003-01-15
EP1138660A4 (en)	2002-10-23
AU755010B2 (en)	2002-11-28
CZ20011368A3 (cs)	2001-08-15
WO2000035843A1 (fr)	2000-06-22
EP1138660A1 (en)	2001-10-04
KR20010086010A (ko)	2001-09-07
CN1329586A (zh)	2002-01-02
NO20012811L (no)	2001-06-07
US6407298B1 (en)	2002-06-18
TW538027B (en)	2003-06-21
AU1411400A (en)	2000-07-03
NZ511022A (en)	2002-06-28
ZA200103328B (en)	2001-10-25
CA2347813A1 (en)	2000-06-22
IL143665A0 (en)	2002-04-21

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KR960000758B1 (ko)	1996-01-12	광학적 활성 히드록시벤질아민 유도체 및 그의 제조방법
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