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

HRID 1608153Notes

Reaction equation

HRID 1608153 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- ; 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-8816e507fb0f4f37a57b5b9f457f394d
Source dataset
uspto-grants-1989_09
Patent number
US04870075

Reaction notes

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