CA1108132A - Process for producing oxymorphone - Google Patents

Process for producing oxymorphone

Info

Publication number: CA1108132A
Authority: CA; Canada
Prior art keywords: demethylating; process according; boron; amount; boron compound
Prior art date: 1978-10-19
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

CA337,908A

Other languages

English (en)

French (fr)

Inventor

Michael L. Wilson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mallinckrodt Inc

Original Assignee

Mallinckrodt Inc

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.)

1978-10-19

Filing date

1979-10-18

Publication date

1981-09-01

1979-10-18 Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc

1981-09-01 Application granted granted Critical

1981-09-01 Publication of CA1108132A publication Critical patent/CA1108132A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 40
UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 title claims abstract description 32
229960005118 oxymorphone Drugs 0.000 title claims abstract description 32
229960002085 oxycodone Drugs 0.000 claims abstract description 36
BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims abstract description 35
239000003795 chemical substances by application Substances 0.000 claims abstract description 32
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 3
239000002879 Lewis base Substances 0.000 claims abstract description 3
229910052796 boron Inorganic materials 0.000 claims abstract description 3
150000007527 lewis bases Chemical class 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 35
230000001335 demethylating effect Effects 0.000 claims description 34
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 32
150000001639 boron compounds Chemical class 0.000 claims description 24
239000012429 reaction media Substances 0.000 claims description 21
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
230000007062 hydrolysis Effects 0.000 claims description 17
238000006460 hydrolysis reaction Methods 0.000 claims description 17
239000012649 demethylating agent Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
239000006227 byproduct Substances 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 8
239000007795 chemical reaction product Substances 0.000 claims description 7
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
230000035484 reaction time Effects 0.000 claims description 5
239000008096 xylene Substances 0.000 claims description 5
238000010520 demethylation reaction Methods 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
238000010791 quenching Methods 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
239000010410 layer Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 5
239000002002 slurry Substances 0.000 description 5
239000008367 deionised water Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
-1 e.g. Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
238000000605 extraction Methods 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000047 product Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910015845 BBr3 Inorganic materials 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000017858 demethylation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
RSSHKMSIEMOBQX-KFIKYVJASA-N (4r,4as,7ar,12bs)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C.O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C RSSHKMSIEMOBQX-KFIKYVJASA-N 0.000 description 1
UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229940023032 activated charcoal Drugs 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
150000001638 boron Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Polarising Elements (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA337,908A 1978-10-19 1979-10-18 Process for producing oxymorphone Expired CA1108132A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US95305678A	1978-10-19	1978-10-19
US953,056		1978-10-19

Publications (1)

Publication Number	Publication Date
CA1108132A true CA1108132A (en)	1981-09-01

Family

ID=25493512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA337,908A Expired CA1108132A (en)	1978-10-19	1979-10-18	Process for producing oxymorphone

Country Status (16)

Country	Link
JP (1)	JPS55501025A (cs)
AU (1)	AU5189779A (cs)
BE (1)	BE879494A (cs)
CA (1)	CA1108132A (cs)
CS (1)	CS211364B2 (cs)
DK (1)	DK258280A (cs)
ES (1)	ES485154A1 (cs)
FI (1)	FI793235A7 (cs)
FR (1)	FR2439201A1 (cs)
GB (1)	GB2049680A (cs)
IL (1)	IL58489A0 (cs)
IT (1)	IT7969032A0 (cs)
NL (1)	NL7920126A (cs)
NO (1)	NO793297L (cs)
SE (1)	SE8004454L (cs)
WO (1)	WO1980000841A1 (cs)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4795813A (en) *	1981-08-17	1989-01-03	The Florida Board Of Regents On Behalf Of The Florida State University	Synthesis of derivatives of codeine and other 3-O-alkylmorphines
US5668285A (en) *	1986-10-31	1997-09-16	The United States Of America As Represented By The Department Of Health And Human Services	Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates
FR2636330B1 (fr) *	1988-09-13	1990-11-30	Sanofi Sa	Procede de preparation de derives de morphinane
DE69033035T2 (de) *	1989-10-16	1999-08-05	The United States of America, represented by the Secretary, U.S. Department of Commerce, Washington, D.C.	Totale synthese von northebain-, normorphin-, noroxymorphon-enantiomeren und -derivaten via n-nor-zwischenverbindungen
US8329216B2 (en)	2001-07-06	2012-12-11	Endo Pharmaceuticals Inc.	Oxymorphone controlled release formulations
KR20030034171A (ko)	2001-07-06	2003-05-01	엔도 파마슈티걸즈, 인크.	옥시모르폰 제어 방출 제형
DK1404331T3 (da)	2001-07-06	2008-01-28	Penwest Pharmaceuticals Co	Sustained release-formuleringer af oxymorphon
US7776314B2 (en)	2002-06-17	2010-08-17	Grunenthal Gmbh	Abuse-proofed dosage system
US20070048228A1 (en)	2003-08-06	2007-03-01	Elisabeth Arkenau-Maric	Abuse-proofed dosage form
DE10336400A1 (de)	2003-08-06	2005-03-24	Grünenthal GmbH	Gegen Missbrauch gesicherte Darreichungsform
DE10361596A1 (de)	2003-12-24	2005-09-29	Grünenthal GmbH	Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
DE102005005446A1 (de)	2005-02-04	2006-08-10	Grünenthal GmbH	Bruchfeste Darreichungsformen mit retardierter Freisetzung
DE102004032049A1 (de)	2004-07-01	2006-01-19	Grünenthal GmbH	Gegen Missbrauch gesicherte, orale Darreichungsform
DE102005005449A1 (de)	2005-02-04	2006-08-10	Grünenthal GmbH	Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
JP5695296B2 (ja)	2006-03-02	2015-04-01	マリンクロッドエルエルシー	低レベルのアルファ，ベータ−不飽和ケトン化合物を伴うモルフィナン−６−オン生成物の製造方法
TWI454288B (zh)	2008-01-25	2014-10-01	Gruenenthal Chemie	藥物劑型
ES2599031T3 (es)	2008-05-09	2017-01-31	Grünenthal GmbH	Proceso para la preparación de una formulación de polvo intermedia y una forma de dosificación solida final utilizando un paso de congelación por pulverización
BR112012001466A2 (pt)	2009-07-22	2020-08-11	Grünenthal GmbH	forma de dosagem resistente à falsificação para opioides sensíveis à oxidação, seu processo de fabricação, e embalagem
ES2534908T3 (es)	2009-07-22	2015-04-30	Grünenthal GmbH	Forma de dosificación de liberación controlada extruida por fusión en caliente
CA2808219C (en)	2010-09-02	2019-05-14	Gruenenthal Gmbh	Tamper resistant dosage form comprising inorganic salt
WO2012028318A1 (en)	2010-09-02	2012-03-08	Grünenthal GmbH	Tamper resistant dosage form comprising an anionic polymer
JP6063462B2 (ja)	2011-07-29	2017-01-18	グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング	即時薬剤放出を提供するタンパーレジスタント錠剤
BR112014002022A2 (pt)	2011-07-29	2017-02-21	Gruenenthal Gmbh	comprimido resistente à violação proporcionando liberação de fármaco imediata
BR112014019988A8 (pt)	2012-02-28	2017-07-11	Gruenenthal Gmbh	Forma de dosagem resistente a socamento compreendendo um composto farmacologicamente ativo e um polímero aniônico
LT2838512T (lt)	2012-04-18	2018-11-12	GrĆ¼nenthal GmbH	Pažeidimui atspari ir dozės atpalaidavimo nuokrypiui atspari farmacinė vaisto forma
US10064945B2 (en)	2012-05-11	2018-09-04	Gruenenthal Gmbh	Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc
MX2015016254A (es)	2013-05-29	2016-04-20	Gruenenthal Gmbh	Forma de dosificacion resistente al uso indebido con perfil de liberacion bimodal.
AU2014273227B2 (en)	2013-05-29	2019-08-15	Grunenthal Gmbh	Tamper-resistant dosage form containing one or more particles
AU2014289187B2 (en)	2013-07-12	2019-07-11	Grunenthal Gmbh	Tamper-resistant dosage form containing ethylene-vinyl acetate polymer
HK1224189A1 (zh)	2013-11-26	2017-08-18	Grünenthal GmbH	通过低温研磨制备粉状药物组合物
WO2015173195A1 (en)	2014-05-12	2015-11-19	Grünenthal GmbH	Tamper resistant immediate release capsule formulation comprising tapentadol
US9872835B2 (en)	2014-05-26	2018-01-23	Grünenthal GmbH	Multiparticles safeguarded against ethanolic dose-dumping
WO2016170097A1 (en)	2015-04-24	2016-10-27	Grünenthal GmbH	Tamper-resistant dosage form with immediate release and resistance against solvent extraction
CA2998259A1 (en)	2015-09-10	2017-03-16	Grunenthal Gmbh	Protecting oral overdose with abuse deterrent immediate release formulations
EP3252055B1 (en)	2016-05-31	2018-09-19	Alcaliber Investigacion Desarrollo e Innovacion SLU	Process for obtaining 3,14-diacetyloxymorphone from oripavine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3249616A (en) *		1966-05-03		Ix-dfflydroxy-g-oxo-n-phenethylmor- phinan (cis) and production thereof
US2806033A (en) *	1955-08-03	1957-09-10	Lewenstein	Morphine derivative
US3775414A (en) *	1972-05-10	1973-11-27	Bristol Myers Co	Process for the preparation of 14-hydroxymorphinan derivatives

1979
- 1979-10-12 NO NO793297A patent/NO793297L/no unknown
- 1979-10-18 JP JP50190279A patent/JPS55501025A/ja active Pending
- 1979-10-18 AU AU51897/79A patent/AU5189779A/en not_active Abandoned
- 1979-10-18 BE BE0/197710A patent/BE879494A/fr unknown
- 1979-10-18 WO PCT/US1979/000862 patent/WO1980000841A1/en not_active Ceased
- 1979-10-18 GB GB8014422A patent/GB2049680A/en not_active Withdrawn
- 1979-10-18 IL IL58489A patent/IL58489A0/xx unknown
- 1979-10-18 CA CA337,908A patent/CA1108132A/en not_active Expired
- 1979-10-18 NL NL7920126A patent/NL7920126A/nl unknown
- 1979-10-18 FR FR7925895A patent/FR2439201A1/fr not_active Withdrawn
- 1979-10-18 FI FI793235A patent/FI793235A7/fi not_active Application Discontinuation
- 1979-10-18 ES ES485154A patent/ES485154A1/es not_active Expired
- 1979-10-18 IT IT7969032A patent/IT7969032A0/it unknown
- 1979-10-19 CS CS797115A patent/CS211364B2/cs unknown
1980
- 1980-06-16 SE SE8004454A patent/SE8004454L/xx not_active Application Discontinuation
- 1980-06-17 DK DK258280A patent/DK258280A/da unknown

Also Published As

Publication number	Publication date
NL7920126A (nl)	1980-08-29
NO793297L (no)	1980-04-22
CS211364B2 (en)	1982-02-26
DK258280A (da)	1980-06-17
SE8004454L (sv)	1980-06-16
BE879494A (fr)	1980-02-15
IT7969032A0 (it)	1979-10-18
JPS55501025A (cs)	1980-11-27
ES485154A1 (es)	1980-06-16
FI793235A7 (fi)	1981-01-01
FR2439201A1 (fr)	1980-05-16
WO1980000841A1 (en)	1980-05-01
GB2049680A (en)	1980-12-31
AU5189779A (en)	1980-04-24
IL58489A0 (en)	1980-01-31

Legal Events

Date	Code	Title	Description
1998-09-01	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 19980901

Publication	Publication Date	Title
WO1980000841A1 (en)	1980-05-01	Process for producing oxymorphone
CA1143751A (en)	1983-03-29	Chemical process
JPH02121993A (ja)	1990-05-09	モルフィナン誘導体の製造方法
US4495353A (en)	1985-01-22	Process for substitution of aromatic organic compounds
US5344980A (en)	1994-09-06	Process for the preparation of 1,3,5-tris(4'-hydroxyaryl)benzene
EP0478559B1 (en)	1996-01-31	Improved process for the preparation of ketone compounds
US4151186A (en)	1979-04-24	Preparation of acyl chlorides
KR900001285B1 (ko)	1990-03-05	브롬화 비페놀의 제조방법
EP0198880B1 (en)	1989-05-31	A method for dealkylation of alkyl-aryl ethers
JP2594826B2 (ja)	1997-03-26	ｐ−またはｍ−ヒドロキシフェネチルアルコールの製造法
JP2585628B2 (ja)	1997-02-26	ハロゲンアルコールの製法
US5440047A (en)	1995-08-08	Method of preparing 2-chloro-pyridinemethanol
KR890005300B1 (ko)	1989-12-20	4,4-비스(4-히드록시페닐)시클로헥산카르복실산유도체의 제조방법
EP0405928B1 (en)	1994-08-31	Process for producing 1,4-dihydroxy-2-arylnaphthoate
US4845301A (en)	1989-07-04	Process for the preparation of α-hdroxyketones
US4460800A (en)	1984-07-17	Process for preparation of hydroxyaryldialkylcarbinols
US5099083A (en)	1992-03-24	Process for preparing 3-chloromethylbenzo-cyclobutene
US4180685A (en)	1979-12-25	Dehydrochlorination of a dihydroxydiphenyl trichloroethane
JP3569428B2 (ja)	2004-09-22	ホモアリルアミン類の製造方法
CA2056979C (en)	1998-06-09	Process for the preparation of ketone compounds
US4246176A (en)	1981-01-20	Synthesis of 5-aroyl-1-hydrocarbylpyrrole-2-acetic acid
US5241103A (en)	1993-08-31	Process for producing 1,4-dihydroxy-2-arylnaphthoate
EP0307106B1 (en)	1992-01-15	P- or m-tert butoxyphenethyl alcohol and process for preparing the same
JPS59137431A (ja)	1984-08-07	トリメチロ−ルヘプタンの製造方法
US4365072A (en)	1982-12-21	Biphenyl aldehydes