Acetic Acid → HCID 178450324, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of fuming nitric acid (0.42), glacial acetic acid (0.27 g) and acetic anhydride (0.27 g) was added dropwise to a solution of 2-butyryl-5-(2,3-dimethylnaphth-1-yl)-3-hydroxy cyclohex-2-en-1-one (1.5 g) in acetic anhydride (8 ml) at 0° C. The mixture was stirred for 1 hr at 5°-10° C. and at 50° C. for 10 min. The cooled mixture was poured into water (150 ml) which was subsequently extracted with ether. The organic fraction was washed successively with a saturated sodium bicarbonate solution and with water. The dried (Na2SO4) organic extract was evaporated under reduced pressure and the residue was purified by column chromatography over silica with dichloromethane elution to give 2-butyryl-3-hydroxy-5-(2,3-dimethyl-4-nitronapth-1-yl)cyclohex-2-en-1-one a yellow foam. Pmr spectrum (CDCl3 ; δ in ppm): 1.03 (3H,t); 1.49-1.89 (2H,m); 2.40-3.89 (6H,m); 2.37 (3H,s); 2.52 (3H,s); 4.06-4.69 (1H,m); 7.32-7.66 (3H,m); 8.00-8.29 (1H,m); 18.38 (1H,s).

Provenance & Evidence