3-(3-Benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester → 3-(3-Hydroxy-phenyl)-2-methoxy-propionic acid methyl ester

Beteiligte Stoffe

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The compounds of 3-(3-benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester (Example 291, Step 3) (3.15 g, 10.49 mmol) and Pd 10% on activated carbon (0.558 g, 0.524 mmol) were placed in a 250-ml round bottom flask equipped with a magnetic stirring bar. 100 mL of methanol was added, and hydrogen was bubbled through the solution for 10 minutes. The flask was sealed with a rubber septum, and a balloon containing 250 mL of hydrogen was connected to the flask through a needle. The mixture was stirred at room temperature for 5 hours and then concentrated to dryness under vacuum. The residue was taken up in ethyl acetate and filtered through a pad of celite. Concentration of the mixture afforded an oil, 1H-NMR (CDCl3, 200.15 MHz): 7.15 (dt, 1H, J=1.1, 7.0), 6.79–6.68 (m, 3H), 5.27 (br s, 1H), 3.98 (dd, 1H, J=7.5, 5.6), 3.73 (s, 3H), 3.35 (s, 3H), 2.97 (d, 1H, J=3.8), 2.97 (d, 1H, J=9.1).

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