Hydrochloric Acid → STK367740

Participants

Reaction Steps

Chromatographed (E),(E)-1,1'-[1,4-phenylene]bis[2-phenyl-1-(diphenylamino)ethylene] (1.0 g, 0.0016 mol) was refluxed in a solution of THF (30 mL) and aqueous HCl (1.2M, 3.0 mL) for 1.25 h. The solution was worked-up as for the preparation of 1,2-diphenylethanone. Chromatography on silica (30 g) eluting with petroleum ether/benzene 3:2 removed the diketone. After solvent evaporation of the combined fractions and recrystallization of the residue from benzene/methanol gave small plates mp 171°-3° C. (85%). FTIR (CDCl3) v: 3089, 3066, 3033, 2900, 1692(C=O), 1676, 1568, 1492, 1454, 1404, 1325, 1309, 1272, 1217, 1202 cm-1H NMR (200 MHz, CDCl3) δ: 4.30 (s, 4H, --CH2Ph), 7.24-7.37 (m, 10H, ending phenyls), 8.06 (s, 4H, phenylene). MS [m/e (70 eV, % of base peak)] C22H18O2 314 (M+. , 0.8), 223 (M+. -PhCH2., 100), 104 (C6H4CO+,42.9), 91 (C7H7+,29).

Provenance & Evidence