HCID 141711, compound → Benzaldehyde, p-phenethyl-

HRID 742783Notes

Reaction equation

HRID 742783 reaction equation
[C:1]1([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[CH2:9]([C:1]1[CH:2]=[CH:3][C:4]([CH:7]=[O:8])=[CH:5][CH:6]=1)[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 141711HCID 141711, compound

Product 1

HCID 121060Benzaldehyde, p-phenethyl-Yield 50.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-stilbenecarboxaldehyde (5.14 g, 24.68 mmol) in 125 mL of ethyl acetate was added 0.13 g of 5% Pd/C catalyst. The reaction was stirred under hydrogen (1 atm) for 2 hours. An additional 0.14 g of 5% Pd/C catalyst was added and the reaction mixture was stirred under hydrogen (1 atm) again for 1 hour. The catalyst was removed by filtration through a pad of Celite. The residue was washed with ethyl acetate (2×30 mL) and the filtrate was concentrated on a rotavap. The residue oil was chromatographed with 15% ethyl acetate in hexanes on silica gel to give 2.62 g (50%) of the desired product as a white solid. 1HNMR (300 MHz, CDCl3) δ9.99 (1H, s), 7.81 (2H, d, J=8.14 Hz), 7.35-7.15 (7H, m), 2.99 (4H, m).

Workup

  1. stirringthe reaction mixture was stirred under hydrogen (1 atm) again for 1 hour
  2. customThe catalyst was removed by filtration through a pad of Celite
  3. washThe residue was washed with ethyl acetate (2×30 mL)
  4. concentrationthe filtrate was concentrated on a rotavap
  5. customThe residue oil was chromatographed with 15% ethyl acetate in hexanes on silica gel

Sources & evidence

ORD record
ord-c42846180fdc4b458500c64add938570
Source dataset
uspto-grants-1996_09
Patent number
US05554767

Reaction notes

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