Methyl 3-Coumarate → Methyl 3-(3-hydroxyphenyl)propionate

HRID 709746Notes

Reaction equation

HRID 709746 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 5352910Methyl 3-Coumarate

Product 1

HCID 1512675Methyl 3-(3-hydroxyphenyl)propionateYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-methyl 3-(3-hydroxyphenyl)acrylate (15.8 g) in methanol (150 mL) was added 10% palladium-activated carbon (1.50 g) and, under a hydrogen atmosphere, the mixture was stirred at room temperature for 5 hr. The reaction mixture was filtered to remove palladium carbon, and the filtrate was evaporated under reduced pressure to give the title compound (16.0 g) as a colorless oil. This compound was used for the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove palladium carbon
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-24aa15e6178c44079e4eddb337eb780f
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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