Acetic Acid → HCID 67017835, compound

Participants

Reaction Steps

To a mixture of NaOH (30.6 g, 765 mmol), H2O (255 mL) and 1,4 dioxane (51 mL) at ice bath temperature was added Br2 (15.2 mL, 285.6 mmol) and stirred for 15 minutes. This hypobromite solution was added dropwise to a stirred solution of 1-{1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]non-3-yl}ethanone (14.5 g, 51.0 mmol) in 1,4-dioxane (51 mL) at ice bath temperature. The reaction mixture was gradually warmed to r.t. and stirred for 1 h. The reaction mixture was cooled to ice bath temperature and quenched by adding AcOH (46.7 mL, 765 mmol). The reaction mixture was diluted with water, extracted with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (8.0 g) as white solid in 55% yield. m/z (M−1), 285; 1H NMR (CDCl3) 300 MHz δ 7.40-7.22 (m, 5H), 4.50 (s, 2H), 3.27 (s, 2H), 2.70-2.62 (m, 1H), 3.47-3.38 (m, 1H), 2.16 (s, 2H), 2.12-1.98 (m, 2H), 1.90-1.55 (m, 7H), 1.50 (dd, J=3.0, 11.0 Hz, 1H).

Provenance & Evidence