Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylate → Methyl (2E)-2-(2-hydroxyphenyl)-3-methoxyprop-2-enoate

HRID 1450157

Reaktionsgleichung

Reaktionsgleichung von HRID 1450157
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17]

Komponenten

5

Edukt 2

HCID 838698Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 14326252Methyl (2E)-2-(2-hydroxyphenyl)-3-methoxyprop-2-enoateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(E)-Methyl 2-(2'-benzyloxyphenyl)-3-methoxyacrylate (5.44 g) was dissolved in ethyl acetate (50 ml) and 5% palladium on carbon (0.25 g) was added. The stirred mixture was hydrogenated at three atmospheres pressure, with stirring, until no more hydrogen was taken up, then filtered through celite and silica gel (50 g, Merck 60). Concentration of the filtrate under reduced pressure afforded (E)-methyl 2-(2'-hydroxyphenyl)-3-methoxyacrylate as a white crystalline solid (3.76 g; 99% yield), mp. 125°-126° C.; infrared max. (nujol mull): 3400, 1670 cm-1 ; 1H NMR (270 MHz): delta 3.80 (3H, s), 3.90 (3H, s), 6.20 (1H, s), 6.80-7.00 (2H,m), 7.10-7.30 (2H,m), 7.60 (1H, s)ppm.

Aufarbeitung

  1. filtrationfiltered through celite and silica gel (50 g, Merck 60)

Quellen und Nachweise

ORD-Eintrag
ord-94e8e48b16ab47ec8e8be8c53ebdce86
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602076

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