Benzyl Bromide → 3-Benzyloxy-4-methoxybenzaldehyde

Participants

Reaction Steps

18--Crown-6 ether (0.14 g, 0.00052 mols) and potassium hydroxide (1.35 g, 0.024 mols) is added to a stirred solution of isovanillin (201) (2.0 g, 0.013 mols) in THF (20 ml) at 0° C. The reacton becomes cloudy and turns bright yellow. Benzyl bromide (1.69 ml, 0.0143 mols) is added dropwise to the reaction at 0° C. After one hour, the ice bath is removed and the reaction is stirred at room temperature overnight. The reaction is diluted with ethyl acetate and washed with water and 10% HCl followed by brine solution. The organic extract is dried over sodium sulfate, filtered, concentrated and dried in vacuo no a yellow crystalline solid (3.0471 g, 96.9%).

Provenance & Evidence