Ammonium Chloride → (4-Benzyloxy-2,6-dichloro-phenyl)methanol

Participants

Reaction Steps

Treat a 0° C. mixture of 2,6-dichloro-4-benzyloxy-benzaldehyde (245 g, 0.871 mol) in ethanol (3 L) with sodium borohydride (32.97 g, 0.897 mol). Warm the reaction to room temperature and stir for 2 hours. Add the reaction mixture to saturated ammonium chloride (8 L). Extract the mixture with CH2Cl2 and dry the organic layer with Na2SO4. Remove the solvent in vacuo to afford 247 g (100%) of the titled product. 1H NMR (400 MHz, DMSO-d6) δ 7.38 (m, 4H), 7.33 (m, 1H), 7.12 (s, 2H), 5.14 (s, 2H), 5.05 (t, 1H), 4.59 (d, 2H).

Provenance & Evidence