3-[4-(3-Benzyloxy-5-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester → 3-[4-(3-Hydroxy-5-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester

HRID 1822284

Reaktionsgleichung

Reaktionsgleichung von HRID 1822284
[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([O:21]CC3C=CC=CC=3)[CH:15]=2)=[CH:9][C:8]=1[CH3:29])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([OH:21])[CH:15]=2)=[CH:9][C:8]=1[CH3:29])[CH3:2]

Komponenten

4

Edukt 1

HCID 690796773-[4-(3-Benzyloxy-5-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

Produkt 1

HCID 578942263-[4-(3-Hydroxy-5-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl esterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-[4-(3-benzyloxy-5-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester (3.56 g, 88.5 mmol) and 10% Pd/C (1.75 g) in ethyl acetate (90 mL) is purged with N2, then purged with H2 and stirred under a hydrogen balloon. Upon completion, the mixture is filtered through hyflo, and the solvent is removed in vacuo to afford 2.83 g (100%) the title compound. Rf=0.35 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C19H22O4 314, found 315 (M+1, 100%).

Aufarbeitung

  1. customis purged with N2
  2. custompurged with H2
  3. filtrationUpon completion, the mixture is filtered through hyflo
  4. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1e52ef37dd8246d3a161635d3a6987ac
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608639B2

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