Hydrochloric Acid → 4,4'-Bis(3-(hydroxymethyl)carbazol-9-yl)biphenyl

Participants

Reaction Steps

Sodium borohydride (2.40 g, 63.4 mmol)) was added to the 4,4′-bis(3-formyl-carbazol-9-yl)biphenyl (3.42 g, 6.33 mmol) in THF (1.2 L) and the resulting suspension was stirred at room temperature for 24 h. (The reaction was followed by TLC using 5% ethanol/dichloromethane as the eluent). Once the reaction was complete, the mixture was slowly poured into water (400 ml) and the mixture was left to stir at room temperature for a further 30 min. The reaction mixture was acidified to pH 1 with hydrochloric acid (5M). The product was extracted with dichloromethane (3×300 ml). The combined organic phase was washed with water (400 ml) and brine (400 ml), dried (MgSO4), filtered and the filtrate evaporated to dryness. The crude product, was purified by chromatography on silica using 50% THF/toluene as the eluent. The product was recrystallised from ethanol to give 4,4′-bis(3-(hydroxy-methyl)carbazol-9-yl) as a pale yellow solid (3.22 g, 94%) with m.p. 268° C. (dec.). Found: C, 82.51; H, 4.64; and N, 4.86. C38H28N2O2. EtOH requires C, 81.33; H, 5.80; N, 4.74%). 1H n.m.r. (300 MHz, MeeSO): δ 8.23 (2H, d, J 7.61 Hz, aromatic H); 8.18 (2H, s, aromatic H); 8.06 (4H, d, J 8.19 Hz, aromatic H); 7.75 (4H, J 8.19 Hz, aromatic H); 7.38-7.50 (8H, m, aromatic H), 7.29 (2H, m, aromatic H); 5.25 (2H, t, J 5.58 Hz, OH); 4.68 (4H, d, J 5.56 Hz, CH2). λmax(CH2Cl2): 216 nm (ε/Lmol−1 cm−1 177 455), 240 (57 873), 271 (56 595), 294 (55 330) 329 (37 758). FTIR (solid): 3343, 1604, 1500, 1485, 1455, 1362, 1330, 1230, 803, 745 cm−1.

Provenance & Evidence