Methyl 4-carboxycinnamate → 4-(3-Methoxy-3-oxopropyl)benzoic acid

HRID 984030Notes

Reaction equation

HRID 984030 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)=[O:4].[H][H]>O1CCOCC1.[Pd]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)=[O:4]

Participants

5

Reactant 2

HCID 54440358Methyl 4-carboxycinnamateHCID 178418361HCID 178418361, compound

Product 1

HCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

8 g (38.8 mmol) of 4-(2-methoxycarbonylvinyl)benzoic acid (step a) were suspended in 250 ml of dioxane and hydrogenated under 1 bar of hydrogen over palladium/charcoal (10%) at room temperature for 7 h. The mixture was filtered and the solvent was evaporated in vacuo. Yield: 8.05 g (100%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-264e2e5f590047e28260ed0233351d01
Source dataset
uspto-grants-2005_03
Patent number
US06867213B2

Reaction notes

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