3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → Dihydroferulic Acid

HRID 2100734Notes

Reaction equation

HRID 2100734 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].[H][H]>CCOC(C)=O.CO.[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

6

Reactant 2

HCID 7093-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 14340Dihydroferulic AcidYield 89.16%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid (20 g, 103 mmol) in EtOAc (100 ml) and MeOH (100 ml) was added carefully 10% Pd/C (2.0 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 and the catalyst was washed with methanol, the filtrate was concentrated and dried at 50° C. under reduced pressure to give product (18 g, 89.16%). LC-MS: m/e 195 (M−1).

Workup

  1. washthe catalyst was washed with methanol
  2. concentrationthe filtrate was concentrated
  3. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-43d38e7df8814fae861c3438a9649beb
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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