3-(3-Hydroxy-4-methoxyphenyl)prop-2-enal → 3-(3-Hydroxy-4-methoxyphenyl)propanal

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-4-methoxycinnamaldehyde (8.66 g, 48.6 mmol) and 5% palladium-alumina (aluminum oxide) (0.540 g) were added to methanol (144 ml), and the mixture was stirred under hydrogen atmosphere of normal pressure (0.1 MPa) at 35° C. for 7 hours for reaction. The reaction solution was filtrated to remove the catalyst, and further the catalyst was washed with methanol (40 ml). The filtrate and the wash solution were combined together, and then concentrated. Thus concentrated solution was subjected to a purification process with a silica gel column chromatography (eluting solvent: toluene/ethyl acetate=4/1). The thus eluted fractions containing the object compound were concentrated under reduced pressure to obtain crude 3-(3-hydroxy-4-methoxyphenyl) propionaldehyde (6.86 g, 38.1 mmol, yield: 78%) in the slightly yellow coloured solid.

Provenance & Evidence