Methanol → Fenoprofen

HRID 851463

Reaktionsgleichung

Reaktionsgleichung von HRID 851463
CS(O[C:6]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:14]=[CH:13][C:7]=1[CH:8]([CH3:12])[C:9]([OH:11])=[O:10])(=O)=O.CO.[H][H]>[Pd].C(N(CC)CC)C>[O:17]([C:16]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 205012982-Methane-sulphonyloxy-3-phenoxy-hydratropic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 3342FenoprofenAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 33 g. of 2-methane-sulphonyloxy-3-phenoxy-hydratropic acid in 200 ml. of methanol 28 ml. of triethyl amine and 2 g. of a 5% palladium on charcoal catalyst are added at 25° C. The mixture is then hydrogenated under atmospheric pressure until a calculated amount of hydrogen is used up. The catalyst is filtered off and the solution is evaporated. The evaporation residue is taken up in water, acidified with a 20% aqueous hydrochloric acid solution and the separated oil is extracted with chloroform. The chloroform solution is evaporated after drying over sodium sulphate, and the residue is distilled off. 23 g. (95%) of 3-phenoxy-hydratropic acid are obtained, boiling at 190° C. to 192° C. (0.4 mmHg.). nD25 =1.5751. Melting point of the corresponding cyclohexylamine salt amounts to 153° C. to 154° C.

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated
  3. extractionthe separated oil is extracted with chloroform
  4. customThe chloroform solution is evaporated
  5. dry with materialafter drying over sodium sulphate
  6. distillationthe residue is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-e3e876e3a56546b5a7f97681e4e1cf34
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04385004

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