Hydrochloric Acid → (3-Chloro-5-methoxyphenyl)methanol

Participants

Reaction Steps

To a solution of 38a (1.0 g, 5.36 mmol, 1.0 equiv.) in 30 mL of THF was added LAH (0.20 g, 5.36 mmol, 1.0 equiv.) in several portions. The mixture was stirred at room temperature for 2 h, and poured into 50 mL of 1M aqueous HCl. The aqueous layer was extracted twice with 30 mL of EtOAc. The combined EtOAc extracts were washed with 40 mL of saturated NaHCO3, 40 mL of brine, dried over Na2SO4, and evaporated in vacuo to give 0.8 g of a white solid. 1H-NMR (DMSO-d6): δ 6.93 (s, 1H), 6.87 (m, 1H), 6.85 (m, 1H), 5.32 (t, J=5.8 Hz, 1H), 4.46 (d, J=6.0 Hz, 2H), 3.76 (s, 3H).

Provenance & Evidence