Methyl 2-(3-phenoxypropenyl)benzoate → Methyl 2-(3-phenoxypropyl)benzoate

HRID 910166Notes

Reaction equation

HRID 910166 reaction equation
[O:1]([CH2:8][CH:9]=[CH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[C].[Pd]>[O:1]([CH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67414986Methyl 2-(3-phenoxypropenyl)benzoate

Product 1

HCID 67413057Methyl 2-(3-phenoxypropyl)benzoateYield 55%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

The thus-obtained methyl 2-(3-phenoxypropenyl)benzoate (0.261 g, 0.972 mmol) was dissolved in methanol (6 ml), 10% palladium carbon (0.022 g) was added, and a hydrogenation reaction was performed at room temperature for 24 hr. The reaction mixture was filtered through celite, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give methyl 2-(3-phenoxypropyl)benzoate (0.144 g, 0.533 mmol, yield 55%).

Workup

  1. customa hydrogenation reaction
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-81897f41f7554283830d72136a92baea
Source dataset
uspto-grants-2011_09
Patent number
US08022072B2

Reaction notes

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