2-Methyl-3-phenylprop-2-enoic acid → alpha-Methylhydrocinnamic acid

HRID 264979

Reaction equation

HRID 264979 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

HCID 145412-Methyl-3-phenylprop-2-enoic acid

Product 1

HCID 99862alpha-Methylhydrocinnamic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

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

  1. filtrationfiltered through a Celite pad in a millipore unit
  2. washwashing the pad well with methanol (2×100 ml.)
  3. customThe clear filtrate was evaporated to dryness
  4. customto give 10.225 g

Sources & evidence

ORD record
ord-32282b74b54342d1868141ab94bdda01
Source dataset
uspto-grants-1997_07
Patent number
US05646276

Linked notes

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