Triphenylphosphine → 3-(3-Hydroxy-4-methoxyphenyl)propanal

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To a chemical reactor for hydrogenation under elevated pressure, 3-(3-hydroxy-4-methoxyphenyl)propionic acid (5.09 g, 25.9 mmol), pivalic acid anhydride (14.3 g, 76.6 mmol) and tetrahydrofuran (64 ml) were introduced, and thereafter the mixture was bubbled with nitrogen gas for 10 minutes. Palladium acetate (57 mg, 0.254 mmol) and triphenyl phosphine (349 mg, 1.33 mmol) were added thereto, and the mixture was bubbled with nitrogen gas for 20 minutes to substitute nitrogen gas completely for the gas in the system of reaction, whereby the system was filled with nitrogen gas. Next, hydrogen gas was added thereinto to substitute hydrogen gas for the gas in the system, and then the mixture was stirred under hydrogen pressure of 5.4 MPa at 80° C. for 24 hours for reaction. Thus obtained reaction solution was concentrated under reduced pressure to remove tetrahydrofaran by distillation. The remaining residue was purified with a silica gel column chromatography. The eluted fractions containing the object compound were concentrated under reduced pressure to obtain crude 3-(3-hydroxy-4-methoxyphenyl)propionaldehyde (2.26 g, 12.5 mmol, yield: 48%) in a slightly yellow colored solid form.

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