2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 2,4-dihydroxy-benzaldehyde (101 g, 0.731 mol) in acetonitrile (700 mL) is treated with KI (12.1 g, 73.1 mmol) and NaHCO3 (70.0 g, 0.834 mol). The mixture is stirred while heating to 60° C. Benzyl chloride (120 g, 0.950 mol) is added and the mixture is refluxed at 82° C. for 16 hours and cooled to room temperature. The solvent is evaporated and the reaction is quenched with water (250 mL) and HCl (5.0 N, 30 mL). The mixture is extracted with EtOAc (300 mL×2), and the organic layers is dried over Na2SO4, filtered, and concentrated to an approximate volume of 200 mL. To 400 mL hexanes is added and the resulting solution is heated to 60° C. to dissolve. The solution is cooled to room temperature and crystallized for 16 hours The solid is filtered and dried to obtain the title compound (130 g, 78%). LC-ES/MS m/e 227.0 (M−1).

Herkunft & Nachweise