2-[4-Hydroxyphenyl]-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester → HCID 21051258, compound

HRID 1270692Notes

Reaction equation

HRID 1270692 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:23])[CH:4]([C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[CH2:5][C:6]1[CH:7]=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1

Participants

3

Reactant 1

HCID 687765982-[4-Hydroxyphenyl]-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester

Product 1

HCID 21051258HCID 21051258, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 3-(3,5-dimethoxy-phenyl)-2-(4-hydroxy-phenyl)-acrylic acid methyl ester (2.1 g) in dioxane (60 mL) 10% palladium on carbon (50% wet, 2.1 g) was added. Hydrogenation was carried out in a Parr shaker at 70 psi for 6.5 h. Catalyst was filtered through a bed of Celite and solvent was evaporated. Yield: quantitative. Analysis: 1HNMR (CDCl3): δ7.15 (d, J=8.7 Hz, 2H), 6.74 (d, J=8.7 Hz, 2H), 6.29 (t, J=2.4 Hz, 1H), 6.25 (d, J=2.4 Hz, 2H), 3.78 (t, J=8.7 Hz, 1H), 3.72 (s, 6H), 3.62(s, 3H), 3.31(dd, J=13.5 & 8.4 Hz, 1H), 2.93 (dd, J=13.5 & 6.9 Hz, 1H).

Workup

  1. additionwas added
  2. filtrationCatalyst was filtered through a bed of Celite and solvent
  3. customwas evaporated

Sources & evidence

ORD record
ord-832bb6e491a24aafa282ec494e23e4e3
Source dataset
uspto-grants-2007_04
Patent number
US07202366B2

Reaction notes

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