Reaction #453787

Reaction equation

4-bromoveratrole

4-(3,4-dimethoxybenzoyl)pyridine

3,5-dimethoxybenzonitrile

butyl lithium

→

3,4,3',5'-Tetramethoxybenzophenone

Conditions

Workup

1. 1
   OtherThe crude product was purified by flash column chromatography (silica gel, methylene chloride)

Procedure

3,4,3',5'-Tetramethoxybenzophenone was prepared analogously to 4-(3,4-dimethoxybenzoyl)pyridine using butyl lithium (9 mL, 22 mmol, 2.5M), 4-bromoveratrole (2.9 mL, 20 mmol) and 3,5-dimethoxybenzonitrile (3.75 g, 23 mmol). The crude product was purified by flash column chromatography (silica gel, methylene chloride) to afford 1.54 g (26%) of the product: mp 107-110° C.; 1H NMR (CDCl3) δ 7.53-7.39 (m, 2 H), 6.95-6.84 (m, 3 H), 6.70-6.60 (m, 1 H), 3.96 (s, 3 H), 3.95 (s, 3 H), 3.83 (s, 6 H); 13C NMR (CDCl3) δ 195.0, 160.4, 153.0, 148.9, 140.1, 130.0, 125.4, 112.0, 109.7, 107.5, 104.1, 56.0, 55.5; Anal. Calcd for C17H18O5. Theoretical: C, 67.54; H, 6.00. Found: C, 67.38; H, 5.96.

Source