Hydrochloric Acid → 1-(4-Nitrophenyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of NaOH (6.3 g, 158.0 mmol), H2O (54.0 mL) and 1,4 dioxane (7 mL) at ice bath temperature was added Br2 (3.2 mL, 59.0 mmol) and stirred for 5 minutes. The formed hypobromite solution was added dropwise to a stirred solution of 1-[1-(4-nitrophenyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone (3.0 g, 10.53 mmol) obtained in step I, in 1,4-dioxane (14 mL) at ice bath temperature. The reaction mixture was gradually warmed to r.t. and after 1 h, it was cooled to ice bath temperature and acidified with conc. HCl, diluted with water, and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-(4-nitrophenyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (2.27 g) in 75% yield as off-white solid; M.R: 145-150° C. m/z (M−1) 286; IR cm−1 3437, 2945, 1693, 1596, 1511, 1408, 1352, 946, 839, 749. 1H NMR (CDCl3) 300 MHz δ 8.16 (d, J=8.8 Hz, 2H), 7.42 (d, J=8.8 Hz, 2H), 2.96-2.88 (m, 1H), 2.59-2.52 (m, 1H), 2.44-2.33 (m, 1H), 2.23-2.03 (m, 4H), 2.02-1.68 (m, 5H).

Provenance & Evidence