Methyl Ferulate → Methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

HRID 1678577Notes

Reaction equation

HRID 1678577 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[O:14][CH3:15]>CO.[C].[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[O:14][CH3:15]

Participants

4

Reactant 1

HCID 5357283Methyl Ferulate

Product 1

HCID 523498Methyl 3-(4-hydroxy-3-methoxyphenyl)propanoateYield 101.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate (3.0 g, 14 mmol) in methanol (30 mL) was added 10% palladium carbon (50% water content, 0.20 g), and the mixture was stirred at room temperature for 4 hours under hydrogen atmosphere. The reaction solution was filtered, and then the filtrate was concentrated under reduced pressure to give the title compound (3.0 g, yield 97%) as an oily matter. The obtained compound was used in the next reaction without purification.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c795cb626f94a5da44697cc230bba21
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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