Ethanol → HCID 18979200, compound

Participants

Reaction Conditions

Reaction Steps

Fuming nitric acid (81 ml) was ice-cooled and acetic anhydride (4.5 ml) was added dropwise. The mixture was cooled to -78° C. and a solution of ethyl 7-(2-naphthyl)heptanoate (10 g) in acetic anhydride (20 ml) was added. The temperature was then increased to -20° C. over a period of 2 hours, after which ethanol (10 ml) was added dropwise. The mixture was stirred for 30 minutes. Then, 2N aqueous sodium hydroxide solution (300 ml) was added under ice-cooling and the mixture was further stirred for 2 hours and, then, extracted with ether. The organic layer was washed with water, dried, and concentrated to dryness. The solid residue (11 g) was added to 5N aqueous sodium hydroxide solution (66 ml)-tetrahydrofuran (264 ml) and the mixture was refluxed for 6 hours. The reaction mixture was acidified with HCl and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated to dryness and the residue was recrystallized from hexane-ethyl acetate to provide 7-(1-nitro-2-naphthyl)heptanoic acid (3.4 g).

Provenance & Evidence