Benzyl Bromide → (4-Benzyloxy-2-hydroxy-phenyl)-(4-benzyloxy-phenyl)-methanone

Participants

Reaction Steps

To a suspension of (2,4-dihydroxy-phenyl)-(4-hydroxy-phenyl)-methanone (9.2 g, 40 mmol) and oven dried potassium carbonate (11.6 g, 84 mmol) in acetone refluxing at 60° C., was added benzyl bromide (10 mL, 83 mmol) in two portions of 5 mL each, dropwise. The reaction was refluxed for 12 hours and solids were filtered and washed with 100 ml of CH7Cl2. The solvents combined and evaporated to give yellow product along with some tribenzylated side product, which was recrystallized from CH2Cl2:hexane (1:5) to get (9.84 g, 60%) of pure product T1. 1H NMR (400 MHz, DMSO-d6) δ, 7.4 (m, 12H, Ar—H2′/6′, 2×C6H5), 6.97 (m, 3H, Ar—H3′/5′, Ar—H6), 5.84 (d, 1H, Ar—H3), 5.6 (dd, 1H, Ar—H5), 5.14 (s, 2H, PhCH2), 4.94 (s, 2H, PhCH2).

Provenance & Evidence