Water → Bis-(3-benzyloxy-4-methoxyphenyl)methanol

Beteiligte Stoffe

Reaktionsschritte

n-BuLi (1.6 M, 5.2 mL) was added to a solution of 2-benzyloxy-4-bromo-1-methoxybenzene (2.10 g, 7.2 mmol) in THF (28 mL) at −78° C. and the resulting yellow solution was stirred at this temperature for 1 h. A solution of 3-benzyloxy-4-methoxybenzaldehyde (1.74 g, 7.2 mmol) in THF (16 mL) was added dropwise at −78° C. and the reaction mixture was stirred at this temperature for 1.5 h and then at room temperature for 2 h. Water (100 mL) was added to the yellow solution and the resulting mixture was extracted with EtOAc (3×100 mL). The combined organics were dried (MgSO4), and solvent was removed in vacuo to give a thick yellow oil which solidified after standing overnight. The crude product was purified by precipitation from EtOAc/hexane to give the title compound (1.70 g, 52%, mp 103-105° C.) as a white solid; δH (270 MHz, CDCl3) 7.42-7.21 (10H, m, ArH), 6.89-6.79 (6H, m, ArH), 5.63 (1H, d, J=3.5, CHOH), 5.06 (4H, s, 2×CH2), 3.86 (6H, s, 2×CH3), 2.02 (1H, d, J=3.5, CHOH); δC (100 MHz, d6-DMSO) 149.2 (2×C), 148.2 (2×C), 137.2 (2×C), 136.6 (2×C), 128.7 (4×CH), 128.0 (2×CH), 127.6 (4×CH), 119.5 (2×CH), 112.6 (2×CH), 111.7 (2×CH), 75.8 (CH), 71.2 (2×CH2), 56.4 (2×CH3); LRMS (FAB+) 456.1 (M+, 45%), 439.1 (85), 349.2 (10), 243.1 (20), 91.1 (100); HRMS (FAB+) Found 456.1944, C29H28O5 requires 456.1937.

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