Ethanol → 3-(4-Tert-butylphenyl)propanoic acid

HRID 1017145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017145
C([C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])(C)(C)C.O1[CH2:20][CH2:19][CH2:18]C1.[H][H].[CH2:23](O)C>[Pd]>[C:19]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:5][C:6]([OH:8])=[O:7])=[CH:15][CH:14]=1)([CH3:18])([CH3:20])[CH3:23]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 54357124t-Butylcinnamic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 49621733-(4-Tert-butylphenyl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A 3 L autoclave was charged with wet t-butylcinnamic acid (248 g, 1.21 mol), tetrahydrofuran (1 L), and ethanol (1 L) and palladium on carbon (35 g). The reactor was shut and 90 psi of hydrogen pressure applied and the reactor held at room temperature overnight. The reaction was then transferred to a round bottom flask and concentrated to 200 mL. The formed crystals were decanted and washed with hexane to give 3-(4-t-butylphenyl)propionic acid (52.9 g after vacuum drying). A second crop from the filtrate yielded additional 3-(4-t-butylphenyl)propionic acid (65.8 g). 1HNMR (CD2Cl2, 500 MHz) δ9.85 (br s, 1H); 7.32 (d, J=8 Hz, 2H); 7.15 (d, JAB=8.5 Hz); 2.91 (t, J=8 Hz, 2H); 2.67 (t, J=8 Hz, 2H); 1.27 (s, 9H).

Aufarbeitung

  1. customThe reaction was then transferred to a round bottom flask
  2. concentrationconcentrated to 200 mL
  3. customThe formed crystals were decanted
  4. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-da68f309293546e392a33db547bf6e40
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479424B1

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