Methyl 3-Coumarate → Methyl 3-(3-hydroxyphenyl)propionate
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe reaction mixture was filtered
- customto remove palladium carbon
- 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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