3-(3,5-Dimethoxyphenyl)prop-2-enoic acid → 3-(3,5-dimethoxyphenyl)propanoic Acid

HRID 2100744Notes

Reaction equation

HRID 2100744 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[H][H]>CCOC(C)=O.CO.[Pd]>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 2

HCID 860923-(3,5-Dimethoxyphenyl)prop-2-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 38702163-(3,5-dimethoxyphenyl)propanoic AcidYield 96.55%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3,5-Dimethoxy-phenyl)-acrylic acid (12 g, 57.7 mmol) in EtOAc (100 ml) and MeOH (100 ml) was added carefully 10% Pd/C (1.3 g), the reaction mixture was shaken in Parr apparatus for 5 hs under 30-40 psi of hydrogen, then the solution was passed through a celite pad, the filtrate was concentrated and dried at 50° C. under reduced pressure to give product (11.7 g, 96.55%). LC-MS: m/e 209 (M−1)

Workup

  1. concentrationthe filtrate was concentrated
  2. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-bb3c3a4adc5149298826fbbfc87413f7
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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