4-(Benzyloxy)-N-methoxy-N-methylbenzamide → 4-Hydroxy-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

10% Palladium on charcoal (4.5 g) in methanol (10 mL) was treated with the product from Example 71B (18.60 g, 68.55 mmol) in 150 mL methanol. The mixture was placed under hydrogen atmosphere at 67 psi. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography to provide the title compound (10.3 g, 83% yield). 1HNMR (300 MHz, CD3OD) δ 3.32 (s, 3H), 3.58 (s, 3H), 6.81 (d, 2H, J=8.9 Hz). 7.59 (d, 2H, J=8.9 Hz); MS (DCI) m/z 182 (M+H)+, 199 (M+NH4)+.

Provenance & Evidence