Thionyl Chloride → 4-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Participants

Reaction Steps

Thionyl chloride (1.85 ml) was added to a solution of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylalcohol (5.00 g) in toluene (40 ml) and the mixture was stirred at room temperature for 30 minutes. Ice water was added to the reaction mixture followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried over MgSO4 and concentrated to give crystals (5.23 g; yield: 99%) of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole. Recrystallization from ethyl acetate-hexane gave colorless crystals. Melting point: 108-109° C.

Provenance & Evidence