Dimethylformamide → 2,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde

Participants

Reaction Steps

To a solution of 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (10.5 g, 32.8 mmol) in Et2O (100 mL) was treated with n-BuLi (28.7 mL, 71.9 mmol) at −78° C. for 1 h. Then, DMF (27.7 mL, 359 mmol) was added to the reaction and the resulting mixture was warmed to room temperature for 3 h. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=2:1) affording the title compound (7.21 g). 1H NMR (300 MHz, CD3OD) δ 10.49 (s, 1H), 7.46 (s, 1H), 6.45 (s, 1H), 5.27 (s, 2H), 5.24 (s, 2H), 4.83 (s, 2H), 3.51 (s, 3H). 3.50 (s, 3H), 3.49 (s, 3H).

Provenance & Evidence