Acetic Acid → 1-Methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid

Participants

Reaction Steps

To a mixture of NaOH (5.8 g, 147 mmol), H2O (40.0 mL) and 1,4 dioxane (10 mL) at ice bath temperature was added Br2 (2.8 mL, 55.0 mmol) and stirred for 5 minutes. The resulting hypobromite solution was added drop-wise to a stirred solution of 1-(1-methoxytricyclo[3.3.1.03,7]non-3-yl)ethanone obtained from step III (1.9 g, 9.8 mmol), in 1,4-dioxane (10 mL) at ice bath temperature. The reaction mixture was gradually warmed to room temperature and stirred for 1 h. The reaction mixture was cooled to ice bath temperature and AcOH (3.9 mL, 65.7 mmol) were added. The reaction mixture was 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-methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid (1.3 g) in 72% yield. m/z (M+1), 197; 1H NMR (CDCl3) 300 MHz δ 3.30 (s, 3H), 2.78-2.70 (m, 1H), 2.57-2.48 (m, 1H), 2.38-2.28 (m, 1H), 2.11-2.0 (m, 2H), 1.86-1.69 (m, 5H), 1.59-1.51 (m, 2H).

Provenance & Evidence