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

HRID 1086994

Reaction equation

HRID 1086994 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b1b567ccf08a4c4ba467b5744d01710b
Source dataset
uspto-grants-1991_07
Patent number
US05034388

Linked notes

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