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

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Reaction Steps

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%).

Provenance & Evidence