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

Temperature

57.5 °C

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%.

1. temperatureThe mixture was heated
2. temperatureThe mixture was cooled
3. stirringAfter stirring for about 5 min
4. stirringthe mixture was stirred at room temperature for 4 hr
5. temperatureUnder ice-cooling
6. temperaturecooling
7. temperatureUnder ice-cooling
8. temperaturecooling at 23° C
9. stirringStirring
10. waitthe reaction mixture was stood overnight at room temperature
11. filtrationThe precipitated solid was collected by filtration
12. washwashed twice with water (150 ml)
13. customThe solid was dried under reduced pressure (40° C.)

ORD record

ord-18bbf811c0de4ec18c839c9aec4bc0c8

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06518435B1