Nitric Acid → HCID 19027049, compound

Participants

Reaction Steps

A solution of 100% nitric acid (0.42 ml, 10 mmol) in 2 ml of acetic anhydride was added dropwise with stirring at <10° to <15° C. to a solution of 8-acetyl-1,2,3,4-tetrahydro5-methoxynaphthalene (2.1 g, 10 mmol) in 25 ml of acetic anhydride containing one drop of conc. sulfuric acid. Stirring was continued for 20 min. at the same temperature, then the reaction mixture was poured into 100 ml of icewater. The precipitated crystals were collected by filtration and washed with water and a small amount of cold ethanol to give 1.48 g (59%) of the title compound. M.p. 76°-77° C.; 1H-NMR (CDCl3) 1.60-1.93 (m, 4H, 2CH2), 2.57 (s, 3H, COCH3), 2.67-3.13 (m, 4H, 2CH2), 3.88 (s, 3H, OCH3), 7.97 (s, 1H, H-7).

Provenance & Evidence