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

Temperature

35 °C

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.

1. filtrationThe reaction solution was filtrated
2. customto remove the catalyst
3. washfurther the catalyst was washed with methanol (40 ml)
4. concentrationconcentrated
5. washThus concentrated solution was subjected to a purification process with a silica gel column chromatography (eluting solvent: toluene/ethyl acetate=4/1)
6. additionThe thus eluted fractions containing the object compound
7. concentrationwere concentrated under reduced pressure

ORD record

ord-809860abc8e24cb6b86d9c695f4bcadc

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06794531B2