CH671014A5 - 4-Hydroxy-4-methoxy:naphthyl-2-butanone prodn. - Google Patents

4-Hydroxy-4-methoxy:naphthyl-2-butanone prodn. Download PDF

Info

Publication number: CH671014A5
Authority: CH; Switzerland
Prior art keywords: methoxy; carried out; acetone; reaction; hydrogenation
Prior art date: 1986-03-21

Application number

CH104887A

Other languages

German (de)

English (en)

Inventor

Dennis Anthony Love

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

1987-03-19

Publication date

1989-07-31

1987-03-19 Application filed by Beecham Group Plc filed Critical Beecham Group Plc

1989-07-31 Publication of CH671014A5 publication Critical patent/CH671014A5/de

Links

CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 46
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
238000006243 chemical reaction Methods 0.000 claims abstract description 22
VZBLASFLFFMMCM-UHFFFAOYSA-N 6-methoxynaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(OC)=CC=C21 VZBLASFLFFMMCM-UHFFFAOYSA-N 0.000 claims abstract description 11
HLOFWGGVFLUZMZ-UHFFFAOYSA-N 4-hydroxy-4-(6-methoxynaphthalen-2-yl)butan-2-one Chemical compound C1=C(C(O)CC(C)=O)C=CC2=CC(OC)=CC=C21 HLOFWGGVFLUZMZ-UHFFFAOYSA-N 0.000 claims abstract description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
239000003054 catalyst Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
238000005984 hydrogenation reaction Methods 0.000 claims description 15
BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
-1 acetic acid) Chemical class 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000002585 base Substances 0.000 claims description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
229910052763 palladium Inorganic materials 0.000 claims description 6
239000000243 solution Substances 0.000 claims description 6
230000008018 melting Effects 0.000 claims description 5
238000002844 melting Methods 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
239000000047 product Substances 0.000 claims description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229960004270 nabumetone Drugs 0.000 claims description 4
238000003756 stirring Methods 0.000 claims description 4
238000004128 high performance liquid chromatography Methods 0.000 claims description 3
238000001953 recrystallisation Methods 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
208000025747 Rheumatic disease Diseases 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
230000002917 arthritic effect Effects 0.000 claims description 2
239000003637 basic solution Substances 0.000 claims description 2
239000013078 crystal Substances 0.000 claims description 2
230000018044 dehydration Effects 0.000 claims description 2
238000006297 dehydration reaction Methods 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
238000001704 evaporation Methods 0.000 claims description 2
230000008020 evaporation Effects 0.000 claims description 2
238000001914 filtration Methods 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
238000002329 infrared spectrum Methods 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
239000002609 medium Substances 0.000 claims description 2
229910000510 noble metal Inorganic materials 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000003791 organic solvent mixture Substances 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims description 2
230000000552 rheumatic effect Effects 0.000 claims description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
JNVOSYBERVWSGY-UHFFFAOYSA-N 4-(6-methoxynaphthalen-2-yl)butan-2-ol Chemical compound C1=C(CCC(C)O)C=CC2=CC(OC)=CC=C21 JNVOSYBERVWSGY-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 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
238000004458 analytical method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material 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

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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)

CH104887A 1986-03-21 1987-03-19 4-Hydroxy-4-methoxy:naphthyl-2-butanone prodn. CH671014A5 (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CH671014A5 true CH671014A5 (en)	1989-07-31

Family

ID=10595051

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH104887A CH671014A5 (en)	1986-03-21	1987-03-19	4-Hydroxy-4-methoxy:naphthyl-2-butanone prodn.

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)

Families Citing this family (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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1474377A (en) *	1973-09-11	1977-05-25	Beecham Group Ltd	Naphthalene derivatives
JPS6045621B2 (ja) *	1978-01-27	1985-10-11	ビ−チヤム・グル−プ・リミテツド	ブタノン誘導体の製造方法

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

Also Published As

Publication number	Publication date
SE8701168D0 (sv)	1987-03-20
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
NL8700656A (nl)	1987-10-16
GB8607119D0 (en)	1986-04-30
ES2004267A6 (es)	1988-12-16

Legal Events

Date	Code	Title	Description
1996-11-15	PL	Patent ceased

Publication	Publication Date	Title
CH628012A5 (de)	1982-02-15	Verfahren zur herstellung von cyklopentenonderivaten.
DE2404160C3 (de)	1981-05-21	Verfahren zur Herstellung von 2-(4-Alkylphenyl)-propionsäuren
DE2404158C3 (de)	1981-02-19	Verfahren zur Herstellung eines 2-(4-Alkylphenyl)-propion-aldehyds
CH671014A5 (en)	1989-07-31	4-Hydroxy-4-methoxy:naphthyl-2-butanone prodn.
DE2105014B2 (de)	1973-03-08	Verfahren zur herstellung von 2,5dimethyl-2,3-dihydrofuran-4-oxy-3-on
CH619955A5 (da)	1980-10-31
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EP0061669B1 (de)	1984-07-25	Verbessertes Verfahren zur Herstellung von Cyclohexan-1,3-dionen sowie einige neue bicyclische Cyclohexan-1,3-dione
DE1951294C3 (de)	1975-08-21	Verfahren zur Herstellung von 3-Hydroxy-2-methyl-y-pyron (Maltol)
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DE2164662A1 (de)	1972-07-27	Indanderivate und Verfahren zu ihrer Herstellung
DE951503C (de)	1956-10-31	Verfahren zur Herstellung von nichtaromatischen monosubstituierten Hydrazinen
DE3037086A1 (de)	1982-05-06	3-(m-chloranilino-)acrylsaeureaethylester und ein verfahren zu dessen herstellung
EP0025939A1 (de)	1981-04-01	Aliphatische Methoxy- und Hydroxynitrile, deren Herstellung und deren Verwendung als Riechstoff
DE3880880T2 (de)	1993-10-07	3-(6'-Methoxy-2'-naphthylmethyl)-2,4-pentandion, Verfahren zur Herstellung und Zwischenprodukte.
CH447147A (de)	1967-11-30	Verfahren zur Herstellung von 5-(3-Hydroxypropyl)-5H-dibenzo(a,d)cycloheptenen
CH629495A5 (de)	1982-04-30	Verfahren zur herstellung von thiophenderivaten und von biotin.
DE2225818A1 (de)	1973-07-05	Verfahren zur erzeugung von beta, delta-dioxoenanthaldehyddialkylacetalen
DE565799C (de)	1932-12-13	Verfahren zur Herstellung von 1-Pheny1-3-methy1-4-alkyl- und -4-aralkylpyrazolonen
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DE1518246C (de)	1972-05-31	Verfahren zur Herstellung von Saccharose estern von substituierten Stearinsäuren
DE837099C (de)	1952-04-21	Verfahren zur Herstellung von Aminodiolen
DE2735600A1 (de)	1979-02-15	Verfahren zur herstellung von phthalid
DE2738016B2 (de)	1980-09-25	Verfahren zur Herstellung von a -Ketocarbonsäuren und die dabei eingesetzten a -Ketocarbonsäureamide
CH362404A (de)	1962-06-15	Verfahren zur Herstellung von a,B-ungesättigten Aldehyden