2-Propenoic acid, 2-methyl-3-phenyl- → alpha-Methylhydrocinnamic acid
Reaction equation
[CH3:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4]>CO.[Pd]>[CH3:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of α-methyl cinnamic acid (10.0 g., 61.7 mmol.) in dry methanol (250 ml.) was treated with 10% palladium on carbon and hydrogenated (balloon used) at room temperature for 16 hours. The reaction mixture was diluted with methanol (250 ml.), filtered through a Celite pad in a millipore unit, washing the pad well with methanol (2×100 ml.). The clear filtrate was evaporated to dryness to give 10.225 g. of title product as a thick syrup.
Workup
- filtrationfiltered through a Celite pad in a millipore unit
- washwashing the pad well with methanol (2×100 ml.)
- customThe clear filtrate was evaporated to dryness
- customto give 10.225 g
Sources & evidence
- ORD record
- ord-2dd08204e1ab4e3cac55386d2d7fb4fa
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723457
Reaction notes
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