Acetic Acid → 2,1-Benzisoxazole

Participants

Reaction Conditions

Reaction Steps

α-Nitrobenzaldehyde (15.1 g, 0.100 mol) and phenol 9.46 (0.100 mol) were dissolved in 120 mL of glacial acetic acid in a three-necked round bottom flask. The flask was flushed with N2 (g), and the solution was cooled to 0° C. HCl (g) was bubbled through the solution and then through a sodium hydroxide solution to neutralize the acid. The reaction flask was fitted with a rubber stopper and the solution was allowed to warm to ambient temperature and then stirred for 2 h. HCl (g) was removed by bubbling N2 (g) through the solution. The resulting precipitate was filtered and washed with 15 mL of glacial acetic acid to afford 16.2 g (66%) of anthranil. The anthranil was directly reduced to 2-Amino-5-chloro-4'-hydroxybenzophenone (below) without further purification.

Provenance & Evidence