4-(4-Hydroxy-1-Butynyl)benzoic Acid Methyl Ester → Methyl 4-(4-hydroxybutyl)benzoate

Participants

Reaction Steps

A Parr flask was charged with 3.25 g (15.98 mmol) of methyl 4-(4-hydroxy-1-butynyl)benzoate (Taylor et al. J. Org. Chem., 1990, 55, 3222-3227) and 0.26 g (8% wt equivalent) of 10% palladium-on-carbon catalyst in 40 mL of ethanol. Hydrogenation was carried out at 50 psi of hydrogen for 18 hours. The mixture was filtered through a silica gel pad that was subsequently washed with ethanol. The combined filtrates were concentrated under reduced pressure to give 3.20 g (97%) of methyl 4-(4-hydroxybutyl)benzoate as a light yellow oil. 1H NMR (CDCl3) δ 1.51 (1H, s), 1.57-1.82 (4H, m), 2.74 (2H, t, J=7.3 Hz), 3.71 (2H, t, J=6.0 Hz), 3.94 (3H, s), 7.27 (2H, d, J=8.0 Hz), 7.99 (2H, d, J=8.0 Hz).

Provenance & Evidence