Sulfuric Acid → 2-(2-Chlorobenzylideneaminooxymethyl)-2-methylpropanoic acid

Participants

Reaction Steps

Concentrated sulfuric acid (4 mL) was added to a stirred mixture of 2-chlorobenzaldehyde (24.5 grams; 0.174 mole) and 4,4-dimethyl-3-isoxazolidinone (20.1 grams; 0.174 mole) in toluene (150 mL) cooled in an ice bath and under a nitrogen atmosphere. Upon completion of addition, the reaction mixture was stirred at ambient temperature overnight under a nitrogen atmosphere. The reaction mixture was then neutralized by the careful addition of solid sodium bicarbonate and then extracted with aqueous sodium bicarbonate (3×500 mL). The combined aqueous extracts were acidified to pH 3 with concentrated hydrochloric acid and then extracted with methylene chloride (3×150 mL). The dried (sodium sulfate) organic layer was concentrated under reduced pressure to afford 16 grams of 2-(2-chlorobenzylideneaminooxymethyl)-2-methylpropanoic acid as a solid, m.p. 78°-80° C.

Provenance & Evidence