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

HRID 1450157

Reaction equation

HRID 1450157 reaction equation
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]

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 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.

Workup

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

Sources & evidence

ORD record
ord-94e8e48b16ab47ec8e8be8c53ebdce86
Source dataset
uspto-grants-1997_02
Patent number
US05602076

Linked notes

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