Formic Acid → 2-(3-nitrophenyl)propanoic Acid

HRID 863205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863205
C(O)=O.Cl[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17].C(N(CC)CC)C>C(#N)C.[Pd]>[N+:16]([C:6]1[CH:7]=[C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])[CH:9]=[CH:10][CH:5]=1)([O-:18])=[O:17]

Komponenten

6

Edukt 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 11064234HCID 11064234, Verbindung

Produkt 1

HCID 111169402-(3-nitrophenyl)propanoic AcidAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

16.5 ml of formic acid are added over 5 minutes to a round-bottomed flask, under inert atmosphere, containing 67.7 g of (RS)-2-(4-chloro-3-nitrophenyl) propionic acid, 87 ml of triethylamine and 6.1 g of 5% palladium-on-charcoal in 680 ml of acetonitrile. The reaction medium is heated at reflux for 18 hours and, after cooling to a temperature in the region of 20° C., is then filtered through Celite. The filtrate is evaporated to dryness under reduced pressure and taken up in 500 ml of water and 400 ml of ethyl acetate. The organic phase is separated out after settling has taken place and the aqueous phase is extracted with twice 200 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated to dryness under reduced pressure at 40° C. 53 g of 2-(3-nitrophenyl)propionic acid are thus obtained in the form of a brown oil [IR spectrum (CH2 Cl2, cm-1) δOH acid: 3250-2450; γCH Aliph.: 2985-2940; γC=0: 1715; γaNO2 : 1535; γsNO2 : 1355; γPh m-subst.: 690; NMR spectrum (DMSO-d6, 200 MHz): 1.45 (d, J=7 Hz, 3H); 3.9 (q, J=7 Hz, 1H); 7.6 (t, J=7 Hz, 1H); 7.8 (d, J=7 Hz, 1H); 8.1 (d, J=7 Hz, 1H); 8.15 (s, 1H); 12.5 (broad s, acidic OH)].

Aufarbeitung

  1. temperatureThe reaction medium is heated
  2. temperatureat reflux for 18 hours
  3. filtrationis then filtered through Celite
  4. customThe filtrate is evaporated to dryness under reduced pressure
  5. customThe organic phase is separated out after settling
  6. extractionthe aqueous phase is extracted with twice 200 ml of ethyl acetate
  7. dry with materialThe combined organic phases are dried over magnesium sulphate
  8. concentrationconcentrated to dryness under reduced pressure at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-bbc2c855b22b4f04b7ff0e02b0055808
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719317

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