Hydrochloric Acid → 4-(2-Hydroxyethyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Next, a mixture of 4-(2-methoxymethoxyethyl)benzaldehyde (8.2 g, 42.1 mmol), methanol (160 mL), water (6 mL) and concentrated hydrochloric acid (4 mL) was stirred at 60° C. for 17.5 hours. After cooling to room temperature, the reaction mixture was neutralized with aqueous sodium hydroxide and evaporated under reduced pressure to remove methanol. The residue was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After concentration, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 50:50) to give 4-(2-hydroxyethyl)benzaldehyde (6.3 g).

Provenance & Evidence