p-Toluenesulfonic acid → HCID 18930726, compound

Participants

Reaction Steps

A mixture of 120c (2.6 g, 8.5 mmol), p-toluene sulfonic acid (1.6 g, 8.5 mmol), 10% Pd/C (0.52 g) and MeOH (40 mL) were shaken on a Parr hydrogenation apparatus at 49 psi of H2. After TLC indicated complete reaction, the catalyst was removed by filtration through a Celite pad, and solvent was evaporated to yield a white solid (3.3 g). IR(KBr): cm-1 3416, 1724. 1H NMR(300 MHz, CDCl3): 8.70 (br, 1H), 7.51-7.28 (m, 6H), 7.12 (d, 2H, J=8 Hz), 4.10 (br, 1H), 3.85 (s, 3H), 3.41-3.24 (m, 8H), 2.29 (s, 3H). HR-MS: Calc'd. 221.1290, Found 221.1294.

Provenance & Evidence