Hydrochloric Acid → 5-methyl-1,3-benzoxazol-2(3H)-one

Participants

Reaction Steps

2-Amino-4-methylphenol (5.00 g, 40.6 mmol) and triethylamine (17 ml, 122 mmol) were dissolved in chloroform (100 ml), ethyl chloroformate (5.8 ml, 61 mmol) was added at room temperature with stirring, and thereafter the mixture was stood at the same temperature overnight. Water was added to the reaction mixture, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. N,N-Dimethylformamide (35 ml) and potassium carbonate (11.2 g, 81.2 mmol) were added to the obtained residue, and the mixture was stirred at 70° C. for 9 hr. The reaction mixture was cooled to room temperature, and 3N hydrochloric acid was added with stirring. The precipitated solid was filtered, washed with water, and dried under reduced pressure to give the title compound (4.94 g, yield 82%) as a pale-bistered solid.

Provenance & Evidence