CH401025A - Verfahren zur Herstellung einer Phenyläthylbenzoesäure - Google Patents

Verfahren zur Herstellung einer Phenyläthylbenzoesäure

Info

Publication number: CH401025A
Authority: CH; Switzerland
Prior art keywords: acid; hydrogen; solution; preparation; phenylethylbenzoic
Prior art date: 1959-08-26

Application number

CH932160A

Other languages

German (de)

English (en)

Inventor

Kollonitsch Janos

Original Assignee

Merck & Co 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.)

1959-08-26

Filing date

1960-08-17

Publication date

1965-10-31

1960-08-17 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1965-10-31 Publication of CH401025A publication Critical patent/CH401025A/de

Links

IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229910052763 palladium Inorganic materials 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000001768 cations Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 9
VQXCRJICWWMTJH-UHFFFAOYSA-N 3-benzyl-3h-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)OC1CC1=CC=CC=C1 VQXCRJICWWMTJH-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
-1 benzalphthalide compound Chemical class 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
YRTPZXMEBGTPLM-UVTDQMKNSA-N (3z)-3-benzylidene-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)O\C1=C/C1=CC=CC=C1 YRTPZXMEBGTPLM-UVTDQMKNSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
HNNSIJBHYRILKJ-UHFFFAOYSA-N 6-oxocyclohexa-2,4-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CC=CC1=O HNNSIJBHYRILKJ-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229910019020 PtO2 Inorganic materials 0.000 description 2
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
229940075564 anhydrous dibasic sodium phosphate Drugs 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
NJXDTGLUPRKMFN-UHFFFAOYSA-N 2-(2-phenylacetyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)CC1=CC=CC=C1 NJXDTGLUPRKMFN-UHFFFAOYSA-N 0.000 description 1
YRTPZXMEBGTPLM-UHFFFAOYSA-N 3-(phenylmethylene)-1-isobenzofuranone Chemical class C12=CC=CC=C2C(=O)OC1=CC1=CC=CC=C1 YRTPZXMEBGTPLM-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
230000000415 inactivating effect Effects 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH932160A 1959-08-26 1960-08-17 Verfahren zur Herstellung einer Phenyläthylbenzoesäure CH401025A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US83605859A	1959-08-26	1959-08-26

Publications (1)

Publication Number	Publication Date
CH401025A true CH401025A (de)	1965-10-31

Family

ID=25271130

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH932160A CH401025A (de)	1959-08-26	1960-08-17	Verfahren zur Herstellung einer Phenyläthylbenzoesäure

Country Status (5)

Country	Link
BE (1)	BE594158A (fr)
CH (1)	CH401025A (fr)
DE (1)	DE1163791B (fr)
ES (1)	ES260649A1 (fr)
GB (1)	GB937378A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS52108957A (en) *	1976-03-04	1977-09-12	Kanzaki Paper Mfg Co Ltd	New process for preparing benzophenone derivatives
DE3211002A1 (de) *	1982-03-25	1983-10-06	Dynamit Nobel Ag	Verfahren zur herstellung von dibenzyl-2-carbonsaeuren und in 3-stellung substituierten phthaliden sowie dabei anfallende neu benzylderivate

1960
- 1960-08-03 DE DEM46132A patent/DE1163791B/de active Pending
- 1960-08-15 GB GB2820160A patent/GB937378A/en not_active Expired
- 1960-08-17 CH CH932160A patent/CH401025A/de unknown
- 1960-08-17 BE BE594158A patent/BE594158A/fr unknown
- 1960-08-20 ES ES0260649A patent/ES260649A1/es not_active Expired

Also Published As

Publication number	Publication date
GB937378A (en)	1963-09-18
BE594158A (fr)	1961-02-17
ES260649A1 (es)	1960-12-16
DE1163791B (de)	1964-02-27

Publication	Publication Date	Title
CH395136A (de)	1965-07-15	Verfahren zur Herstellung von Xanthenen oder Thiaxanthenen
CH401025A (de)	1965-10-31	Verfahren zur Herstellung einer Phenyläthylbenzoesäure
EP0176026A1 (fr)	1986-04-02	Procédé pour la préparation de l'acide 2,4-dichloro-5-fluoro-benzoique
EP0008118B1 (fr)	1981-01-07	Procédé de préparation de 3,3-bis-(4-diméthylaminophényl)-6-diméthylaminophtalide
DE2215048C3 (de)	1982-04-01	Verfahren zur Herstellung von 2-[Bis-(4,4'-dialkylamino)-benzhydryl)-5-aminobenzoesäuren
AT323154B (de)	1975-06-25	Verfahren zur herstellung von neuen 5-methoxy-2-methylindol-3-essigsäurederivaten sowie von deren salzen
AT294047B (de)	1971-11-10	Verfahren zur Herstellung von Bis-alkanolaminderivaten und deren Salzen
AT212470B (de)	1960-12-27	Verfahren zur Herstellung von neuen Oxydationsfarbstoffen
AT233744B (de)	1964-05-25	Verfahren zur Herstellung von Reserpsäureestern sowie deren Salzen
AT224128B (de)	1962-11-12	Verfahren zur Herstellung von neuen Phosphorsäureestern
AT245729B (de)	1966-03-10	Verfahren zur Gewinnung von sedativ und spasmolytisch wirksamen Estern aus Radix valerianae
AT281005B (de)	1970-05-11	Verfahren zur Herstellung von neuen o-Aroylaminoaryloxyessigsäuren
AT211817B (de)	1960-11-10	Verfahren zur Herstellung von β-Lactonen
DE2049941C (de)	1973-04-05	Verfahren zur Herstellung von 2 De carboxamido 2 lminotetracychnen, bzw ihren Saureadditionssalzen oder Metallsalzen
AT203509B (de)	1959-05-25	Verfahren zur Herstellung von neuen, substituierten 3,5-Dioxo-tetrahydro-1,2,6-thiadiazin-1,1-dioxyden
DE825548C (de)	1951-12-20	Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen
AT372375B (de)	1983-09-26	Verfahren zur herstellung von neuen 1,3-thiazol- verbindungen und von deren salzen
AT384020B (de)	1987-09-25	Verfahren zur herstellung von 6-methyl-4-hydroxynicotinsaeure
AT267527B (de)	1969-01-10	Verfahren zur Herstellung neuer substituierter Aminopyridine, von deren Salzen und optisch aktiven Isomeren
DE883156C (de)	1953-07-16	Verfahren zur Herstellung von 2-Amino-4-sulfamido-phenylarsinsaeure
AT222806B (de)	1962-08-10	Verfahren zur Herstellung von Aminoestern des Penicillins und von Salzen derselben
AT211816B (de)	1960-11-10	Verfahren zur Herstellung von neuen polyjodierten Benzoylverbindungen
AT284126B (de)	1970-09-10	Verfahren zur Herstellung neuer substituierter Aminopyrimidine und deren Salze und optisch aktiven Isomere
AT366381B (de)	1982-04-13	Verfahren zur herstellung von n-(3-(1'-3''oxapentamethylenamino-aethylidenamino)-2,4,6-
EP1102738B1 (fr)	2002-12-04	Procede de saponification acide ou alcaline de biphenylnitriles