NL8700656A - Nieuwe werkwijze. - Google Patents

Nieuwe werkwijze. Download PDF

Info

Publication number: NL8700656A
Authority: NL; Netherlands
Prior art keywords: process according; acetone; methoxy; naphthaldehyde; takes place
Prior art date: 1986-03-21

Application number

NL8700656A

Other languages

English (en)

Dutch (nl)

Original Assignee

Beecham Group Plc

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.)

1986-03-21

Filing date

1987-03-20

Publication date

1987-10-16

1987-03-20 Application filed by Beecham Group Plc filed Critical Beecham Group Plc

1987-10-16 Publication of NL8700656A publication Critical patent/NL8700656A/nl

Links

238000000034 method Methods 0.000 title claims description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 8
238000005984 hydrogenation reaction Methods 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
RQSRLHYBIGCTIS-UHFFFAOYSA-N 6-methoxynaphthalene-1-carbaldehyde Chemical compound O=CC1=CC=CC2=CC(OC)=CC=C21 RQSRLHYBIGCTIS-UHFFFAOYSA-N 0.000 claims 4
239000003960 organic solvent Substances 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
150000001875 compounds Chemical class 0.000 description 5
BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 description 4
229960004270 nabumetone Drugs 0.000 description 4
239000002253 acid Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 2
-1 acetic acid) Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
MLFCHYYDLUDPLW-UHFFFAOYSA-N 7-methoxynaphthalene-2-carbaldehyde Chemical compound C1=CC(C=O)=CC2=CC(OC)=CC=C21 MLFCHYYDLUDPLW-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation

Landscapes

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

NL8700656A 1986-03-21 1987-03-20 Nieuwe werkwijze. NL8700656A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8607119		1986-03-21
GB868607119A GB8607119D0 (en)	1986-03-21	1986-03-21	Process

Publications (1)

Publication Number	Publication Date
NL8700656A true NL8700656A (nl)	1987-10-16

Family

ID=10595051

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8700656A NL8700656A (nl)	1986-03-21	1987-03-20	Nieuwe werkwijze.

Country Status (8)

Country	Link
JP (1)	JPS62230744A (da)
CH (1)	CH671014A5 (da)
DK (1)	DK142387A (da)
ES (1)	ES2004267A6 (da)
GB (1)	GB8607119D0 (da)
GR (1)	GR870454B (da)
NL (1)	NL8700656A (da)
SE (1)	SE8701168L (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5756851A (en) *	1996-10-21	1998-05-26	Albemarle Corporation	Production of nabumetone or precursors thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2242972A1 (da) *	1973-09-11	1975-04-04	Beecham Group Ltd
EP0003643A1 (en) *	1978-01-27	1979-08-22	Beecham Group Plc	Process for the preparation of 4-(6-methoxy-2-naphthyl)-butan-2-one; 4-(6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one and a process for its preparation

1986
- 1986-03-21 GB GB868607119A patent/GB8607119D0/en active Pending
1987
- 1987-03-19 GR GR870454A patent/GR870454B/el unknown
- 1987-03-19 DK DK142387A patent/DK142387A/da not_active Application Discontinuation
- 1987-03-19 CH CH104887A patent/CH671014A5/de not_active IP Right Cessation
- 1987-03-20 NL NL8700656A patent/NL8700656A/nl not_active Application Discontinuation
- 1987-03-20 SE SE8701168A patent/SE8701168L/xx not_active Application Discontinuation
- 1987-03-20 ES ES8700790A patent/ES2004267A6/es not_active Expired
- 1987-03-20 JP JP6773787A patent/JPS62230744A/ja active Pending

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2242972A1 (da) *	1973-09-11	1975-04-04	Beecham Group Ltd
EP0003643A1 (en) *	1978-01-27	1979-08-22	Beecham Group Plc	Process for the preparation of 4-(6-methoxy-2-naphthyl)-butan-2-one; 4-(6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one and a process for its preparation

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 090, no. 1, 1 January 1979, Columbus, Ohio, US; abstract no. 000223, GOUDIE A C ET AL: "4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds" *
CHEMICAL ABSTRACTS, vol. 103, no. 17, 28 October 1985, Columbus, Ohio, US; abstract no. 141569, LIU K ET AL: "Synthesis of nabumetone" *
J. MED. CHEM. (JMCMAR,00222623);78; VOL.21 (12); PP.1260-4, BEECHAM PHARM.;MED. RES. CENT.; HARLOW/ESSEX; ENGL. *
YIYAO GONGYE (YIGODN);85; VOL.16 (4); PP.147-9, JIANGSU PHARM. IND. CO.;PEOP. REP. CHINA (CN) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5756851A (en) *	1996-10-21	1998-05-26	Albemarle Corporation	Production of nabumetone or precursors thereof
US5907069A (en) *	1996-10-21	1999-05-25	Albemarle Corporation	Production of nabumetone or precursors thereof

Also Published As

Publication number	Publication date
SE8701168D0 (sv)	1987-03-20
CH671014A5 (en)	1989-07-31
SE8701168L (sv)	1987-09-22
DK142387D0 (da)	1987-03-19
JPS62230744A (ja)	1987-10-09
GR870454B (en)	1987-07-10
DK142387A (da)	1987-09-22
GB8607119D0 (en)	1986-04-30
ES2004267A6 (es)	1988-12-16

Legal Events

Date	Code	Title
1994-05-02	BA	A request for search or an international-type search has been filed
1995-04-03	BB	A search report has been drawn up
1995-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0370461B1 (en)	1995-06-28	Chalcone derivatives and process for producing the same
JP2830211B2 (ja)	1998-12-02	β−ヒドロキシケトン類の製造方法
US4877909A (en)	1989-10-31	Process for reducing aldehydes or ketones
US5274145A (en)	1993-12-28	α-hydroxy-acids, preparation process and the use thereof
NL8700656A (nl)	1987-10-16	Nieuwe werkwijze.
US3387003A (en)	1968-06-04	Process for the production of 3-methyl-2-cyclopentene-4-ol-1-ones
Serota et al.	1981	Novel synthesis of. alpha.-substituted acrylic acids
Bidd et al.	1983	Convenient syntheses of bifunctional C 12-acyclic compounds from cyclododecanone
US2780645A (en)	1957-02-05	Preparation of calcium dl-pantothenate
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US4517382A (en)	1985-05-14	1-Formyl-tri- and tetramethyl-cyclohex-1-en-3-one oximes
US3825572A (en)	1974-07-23	Epimeric mixtures of the lactone 3,6-dihydro-4,5-dimethyl-5-phenyl-alpha-pyrone
US3845076A (en)	1974-10-29	Method of preparing aldehydes
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US3280191A (en)	1966-10-18	Method for preparing dihydroxyacetone
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