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

Participants

Reaction Steps

To a stirring solution of 4-(4-hydroxy-but-1-ynyl)-benzoic acid methyl ester (6.29 g, 0.031 mol) in ethanol (60 mL) was added palladium on carbon (5 g, 10% on carbon) and the reaction mixture was hydrogenated at 50 psi. After 20 hours, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated to afford 4-(4-hydroxy-butyl)-benzoic acid methyl ester (5.67 g, 0.027 mol) as the desired product (89% yield). 1H (CDCl3, 600 MHz): δ 7.94 (2H, d, J=8.4 Hz), 7.24 (2H, d, J=8.4 Hz), 3.89 (s, 3H), 3.65 (2H, t, J=6.6 Hz), 2.65 (2H, t, J=7.8 Hz), 1.71 (2H, m), 1.58 (2H, m).

Provenance & Evidence