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

HRID 1086994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1086994
[CH3:1][O:2]/[CH:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]CC1C=CC=CC=1)/[C:5]([O:7][CH3:8])=[O:6].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2]/[CH:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])/[C:5]([O:7][CH3:8])=[O:6]

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 3-methoxy(2'-benzyloxyphenyl)propenoate (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 3-methoxy-2-(2'-hydroxyphenyl)propenoate as a white crystalline solid (3.76 g; 99% yield), M.P. 125-126° C.; infrared maxima (nujol mull): 3400, 1670 cm-1 ; 1H nmr (CDCl3, 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-b1b567ccf08a4c4ba467b5744d01710b
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034388

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