Benzene → (4E)-2,4-dimethyl-5-phenyl-4-pentenal

HRID 2408255Notes

Reaction equation

HRID 2408255 reaction equation
C([O:4][CH2:5]/[C:6](/[CH3:14])=[CH:7]/[C:8]1[CH:13]=CC=C[CH:9]=1)C=C.[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:14][CH:6]([CH2:7]/[C:8](/[CH3:13])=[CH:9]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:5]=[O:4]

Participants

3

Reactant 2

HCID 241BenzeneHCID 67330776(1E)-[3-(allyloxy)-2-methyl-1-propenyl]benzene

Product 1

HCID 58390606(4E)-2,4-dimethyl-5-phenyl-4-pentenalYield 10%

Procedure

The (1E)-[3-(allyloxy)-2-methyl-1-propenyl]benzene (107.79 g, 0.571 mol), [RuCl2(PPh3)3] (3.13 g), BHT (1 g) and benzene (500 ml) were heated together in an autoclave in an oil bath at 190° C. for 4 hours. After cooling to room temperature, solvents were evaporated and the product purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 10:1) followed by bulb-to-bulb distillation (88° C./0.009 mbar) to give 11.21 g of the desired compound (0.060 mol, 10%).

Workup

  1. customsolvents were evaporated
  2. customthe product purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 10:1)
  3. distillationfollowed by bulb-to-bulb distillation (88° C./0.009 mbar)

Sources & evidence

ORD record
ord-091e91c37da045819fed165a702cda8f
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

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