Toluene → 4-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Participants

Reaction Conditions

Reaction Steps

{4-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}-methanol (300 g), tetrahydrofuran (750 ml) and toluene (750 ml) were charged and the mixture was cooled to 5° C. Thionyl chloride (88 ml) was added dropwise at not higher than 15° C. over 10 min and the mixture was reacted at 10-15° C. for 1 hr. 10% Brine (900 ml) was added dropwise at the same temperature over about 10 min, and the mixture was stood for 30 min, partitioned and activated carbon (15 g) was added to the organic layer. The mixture was stirred for about 1 hr, and the activated carbon was filtered off and the mixture was washed with toluene (300 ml). The organic layer was concentrated to about 805 g and then heated to about 60° C. to dissolve crystals, followed by standing for cooling. The mixture was cooled to about 25° C. over 30 min and n-hexane (1800 ml) was added dropwise over about 30 min. The mixture was cooled to around 5° C. and aged for 1 hr. The crystals were collected by filtration and washed with cold toluene-n-hexane (1:3) (600 ml). The crystals were dried under reduced pressure at 40° C. to give pale-yellow 4-{[4-(chloromethyl)phenoxy]methyl}-5-methyl-2-phenyl-1,3-oxazole (280.0 g) in a yield of 87.9%.

Provenance & Evidence