HCID 57712919, compound → 5-(2,4-dimethoxyphenyl)pentanoic acid

Participants

Reaction Steps

A 1-L hydrogenation flask was charged with 36.2 g of 5-(2,4-dimethoxyphenyl)-4-pentenoic acid (3a) and 400 ml of glacial acetic acid. The flask was flushed with argon and 2 g of (10% Pd/C) were added to the flask, which was then attached to the hydrogenator. The hydrogenation bottle was evacuated, and charged with hydrogen to 40 to 50 psi. The reaction was run overnight until no further hydrogen was being consumed. The solution was filtered through Cellite (diatomaceous earth). The solvent was evaporated, and the residue dried in vacuo. The yield was 99%. 1H NMR (DMSO-d6) δ: 12.01 (br s, 1H), 6.99 (d, J=8.2 Hz, 1H), 6.49 (d, J=2 Hz, 1H), 6.41 (dd, J1=2 Hz, J2=8.2 Hz, 1H), 3.74 (s, 3H), 3.72 (s, 3H), 2.45 (t, 2H), 2.20 (t, 2H), 1.47 (m, 4H).

Provenance & Evidence