Acetic Acid → 2-(4-Chlorophenyl)-4,5-dimethyl-1,3-oxazol 3-oxide

Participants

Reaction Steps

1.00 g (9.89 mmol) of diacetyl monoxime and 1.53 g (10.88 mmol) of 4-chlorobenzaldehyde were initially charged in 2 ml (34.94 mmol) of glacial acetic acid. Then, while the reaction mixture was cooled with ice, hydrogen chloride gas was introduced for 30 min. 10 ml of diethyl ether were then added to the reaction mixture. A precipitate was formed which was filtered off and washed twice with in each case 2 ml of diethyl ether. The precipitate was resuspended in about 5 ml of water and the suspension was made basic using 25% strength aqueous ammonia solution. The mixture was extracted four times with in each case 10 ml of dichloromethane. The combined organic phases were dried over magnesium sulfate and the solvent was removed on a rotary evaporator. Without further purification, the residue was used for the next reaction.

Provenance & Evidence