Pyrogallol → 1,1',1''-[Benzene-1,2,3-triyltris(oxymethylene)]tribenzene

Participants

Reaction Steps

Lowe, W. et al., Arch. Pharm. (Weinheim) 327:255 (1994). Benzyl bromide (57 mL, 0.481 mol) and then K2CO3 (100 g, 0.725 mol) were added to a solution of pyrogallol (20 g, 0.1 59 mol) in 200 mL dry, degassed acetone under Ar. This reaction mixture was subsequently stirred for 30 min at room temperature and then for 24 h at reflux under Ar. A solution of NaOH (1.6 g) in MeOH (32 mL) was then added and the reaction refluxed for an additional 30 min. After cooling to room temperature, solids were filtered and washed with acetone. The filtrate was concentrated and the residue recrystallized from MeOH to afford 8 (52 g, 83%) as an off-white solid. mp 67-68° C. 1H NMR (CDCl3): δ7.44-7.19 (m, 15 H), 6.85 (dd, J=9, 9 Hz, 1 H), 6.57 (d, J=8.2 Hz, 2 H), 5.05 (s, 2 H), 5.02 (s, 4 H). 13C NMR (CDCl3): δ152.9, 138.4, 137.8, 137.0, 128.4, 128.3, 128.0, 127.8, 127.6 (2), 127.3, 127.2, 123.5, 107.7, 75.0, 70.9.

Provenance & Evidence