Hydrochloric Acid → 4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

4-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole (50.0 g) was dissolved in dimethyl acetamide (200 ml) and parahydroxybenzaldehyde (30.9 g) and potassium carbonate (49.9 g) were added at room temperature. The mixture was heated and stirred at 50-65° C. for 4 hr. The mixture was cooled, and sodium borohydride (9.11 g) was added at 5-13° C. After stirring for about 5 min, the mixture was stirred at room temperature for 4 hr. Under ice-cooling, methanol (50 ml) was added at 20-21° C., and water (50 ml) was added at 21-24° C. under ice-cooling. Under ice-cooling, conc. hydrochloric acid (50 ml) was added at 18-25° C. and water (50 ml) was added under ice-cooling at 23° C. Stirring was stopped and the reaction mixture was stood overnight at room temperature. The precipitated solid was collected by filtration and washed twice with water (150 ml). The solid was dried under reduced pressure (40° C.) to give {4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}methanol (68.3 g) as a pale-yellow brown solid in a yield of 96.0%.

Provenance & Evidence