CA1037061A - Production d'acetonaphtones ortho-hydroxy-w-(methylsulfinyle) - Google Patents

Production d'acetonaphtones ortho-hydroxy-w-(methylsulfinyle)

Info

Publication number: CA1037061A
Authority: CA; Canada
Prior art keywords: hydroxy; naphthoate; tetrahydro; process according; lower alkyl
Prior art date: 1973-08-27
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

CA206,772A

Other languages

English (en)

Other versions

CA206772S (en

Inventor

Maximilian Von Strandtmann

John Shavel (Jr.)

Sylvester Klutchko

Marvin P. Cohen

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.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

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.)

1973-08-27

Filing date

1974-08-12

Publication date

1978-08-22

1973-08-27 Priority claimed from US00392152A external-priority patent/US3843730A/en

1974-08-12 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1978-08-22 Application granted granted Critical

1978-08-22 Publication of CA1037061A publication Critical patent/CA1037061A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 25
150000001875 compounds Chemical class 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
239000002244 precipitate Substances 0.000 claims description 10
159000000000 sodium salts Chemical class 0.000 claims description 10
239000000047 product Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 5
239000012312 sodium hydride Substances 0.000 claims description 5
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
239000012454 non-polar solvent Substances 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 2
230000001376 precipitating effect Effects 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
-1 alkyl 5,6,7,8-tetrahydro-3-hydroxy-2-naphthoate Chemical compound 0.000 claims 5
239000000126 substance Substances 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
206010027654 Allergic conditions Diseases 0.000 abstract description 2
206010020601 Hyperchlorhydria Diseases 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
150000004777 chromones Chemical class 0.000 abstract 1
239000000203 mixture Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
229940076134 benzene Drugs 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
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 3
229960000583 acetic acid Drugs 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FWLIEUDMZIYEAW-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-2-methylsulfinylethanone Chemical compound CS(=O)CC(=O)C1=CC=CC=C1O FWLIEUDMZIYEAW-UHFFFAOYSA-N 0.000 description 1
NLVBCDOAWYJCLV-UHFFFAOYSA-N 1-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid Chemical compound C1CCCC2=C(O)C(C(=O)O)=CC=C21 NLVBCDOAWYJCLV-UHFFFAOYSA-N 0.000 description 1
QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical class C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 1
UOBYKYZJUGYBDK-UHFFFAOYSA-M 2-naphthoate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-M 0.000 description 1
LSHXXOVEYBIVIW-UHFFFAOYSA-N 3-(hydroxymethyl)benzo[h]chromen-4-one Chemical compound C1=CC=CC2=CC=C(C(C(CO)=CO3)=O)C3=C21 LSHXXOVEYBIVIW-UHFFFAOYSA-N 0.000 description 1
RSWXAGBBPCRION-UHFFFAOYSA-N 5,6,7,8-tetrahydro-2-naphthoic acid Chemical compound C1CCCC2=CC(C(=O)O)=CC=C21 RSWXAGBBPCRION-UHFFFAOYSA-N 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
150000008062 acetophenones Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
AMBJIFDYCIFVBA-UHFFFAOYSA-N methyl 1-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate Chemical compound C1CCCC2=C(O)C(C(=O)OC)=CC=C21 AMBJIFDYCIFVBA-UHFFFAOYSA-N 0.000 description 1
YRGJVRHNWPDXMH-UHFFFAOYSA-N methyl 3-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate Chemical compound C1CCCC2=C1C=C(C(=O)OC)C(O)=C2 YRGJVRHNWPDXMH-UHFFFAOYSA-N 0.000 description 1
229960001047 methyl salicylate Drugs 0.000 description 1
VLGWYKOEXANHJT-UHFFFAOYSA-N methylsulfanol Chemical compound CSO VLGWYKOEXANHJT-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CA206,772A 1973-08-27 1974-08-12 Production d'acetonaphtones ortho-hydroxy-w-(methylsulfinyle) Expired CA1037061A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US00392152A US3843730A (en)	1971-08-25	1973-08-27	Ortho-hydroxy-omega-(methylsulfinyl-)acetonaphthones and process for producing same

Publications (1)

Publication Number	Publication Date
CA1037061A true CA1037061A (fr)	1978-08-22

Family

ID=23549462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA206,772A Expired CA1037061A (fr)	1973-08-27	1974-08-12	Production d'acetonaphtones ortho-hydroxy-w-(methylsulfinyle)

Country Status (5)

Country	Link
JP (1)	JPS5245708B2 (fr)
CA (1)	CA1037061A (fr)
DK (1)	DK410974A (fr)
FR (1)	FR2242378B1 (fr)
GB (1)	GB1416669A (fr)

1974
- 1974-08-01 DK DK410974A patent/DK410974A/da unknown
- 1974-08-12 CA CA206,772A patent/CA1037061A/fr not_active Expired
- 1974-08-12 GB GB3540874A patent/GB1416669A/en not_active Expired
- 1974-08-19 FR FR7428420A patent/FR2242378B1/fr not_active Expired
- 1974-08-20 JP JP49094663A patent/JPS5245708B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2436943B2 (de)	1976-01-15
JPS5245708B2 (fr)	1977-11-17
DK410974A (fr)	1975-04-28
JPS50105645A (fr)	1975-08-20
FR2242378A1 (fr)	1975-03-28
AU7208074A (en)	1976-02-12
GB1416669A (en)	1975-12-03
DE2436943A1 (de)	1975-03-27
FR2242378B1 (fr)	1976-12-31

Publication	Publication Date	Title
US2398418A (en)	1946-04-16	Introduction of organic radicals into quinones
US4728743A (en)	1988-03-01	Process for the production of 3-oxonitriles
US5900517A (en)	1999-05-04	Cyclopentadienyl derivatives and process for their preparation
NO143531B (no)	1980-11-24	Fremgangsmaate for fremstilling av acylerte benzoksazolinon-derivater
CA1037061A (fr)	1978-08-22	Production d'acetonaphtones ortho-hydroxy-w-(methylsulfinyle)
US2752360A (en)	1956-06-26	Improvement in the manufacture of 3-substituted 4-hydroxycoumarins
DeTar et al.	1955	The thermal decomposition of 2-phenoxybenzoyl peroxide
DE2726393C2 (de)	1984-04-12	Verfahren zur Herstellung von 5-(quartär-Alkyl)resorcinen
US2827489A (en)	1958-03-18	Process for the preparation of 2-diphenylacetyl-1, 3-indandione
US3564016A (en)	1971-02-16	Method of decarbonylation
DE60204681T2 (de)	2006-05-18	Verfahren zur herstellung von 2-[4-(2,2,-dihalocyclopropyl)phenoxy]-alkansäuren und ihre estern
US4201715A (en)	1980-05-06	Process for the anilidization of carboxylic acid esters
US3931322A (en)	1976-01-06	Synthesis of 2-alkyl-cyclopentan-1,3-diones
US4873363A (en)	1989-10-10	Process for the preparation of 3-(4'-bromobiphenyl-4-yl)tetralin-1-one
US5233082A (en)	1993-08-03	Method of making 3-hydroxy-2,4,5-trifluorobenzoic acid
US3843730A (en)	1974-10-22	Ortho-hydroxy-omega-(methylsulfinyl-)acetonaphthones and process for producing same
FR2663032A1 (fr)	1991-12-13	Procede de preparation de derives de 2-phenyl-6-(pyrimidine-2-yl) pyridine.
Kant et al.	1984	Reissert compound studies. XLV. The phenanthridine reissert compound
DE1076133B (de)	1960-02-25	Verfahren zur Herstellung von ª‡,ª‡'-(Diacyl)-bis-ketocarbon-saeureestern
US3019233A (en)	1962-01-30	5-hydroxy-2-oxyphenylcyclopentane-alkanols and intermediates
US4451658A (en)	1984-05-29	Process for producing substituted pyrroles
DE2436943C3 (de)	1976-09-02	o-Hydroxy-omega-(methylsulfinyl)acetonaphthone und Verfahren zu ihrer Herstellung
JPH078816B2 (ja)	1995-02-01	ジベンゾイルメタンの製造法
US5284975A (en)	1994-02-08	Method of preparing α-d-phenylalkylbenzyl carbinol
DE2302970A1 (de)	1973-08-02	Verfahren zur herstellung heterocyclischer verbindungen