Acetic Acid → HCID 67300448, compound

Participants

Reaction Steps

To a mixture of NaOH (10.8 g, 270 mmol), H2O (72 mL) and 1,4-dioxane (20 mL) at ice bath temperature was added Br2 (5.2 mL, 100.8 mmol) and stirred for 5 minutes. This hypobromite solution was added drop-wise to a solution of the compound obtained from step III (4.84 g, 18 mmol) in 1,4-dioxane (18 mL) kept at ice bath temperature. The reaction mixture was gradually warmed to room temperature and stirred for 1 h, after which it was cooled to ice bath temperature and quenched by adding AcOH (3.9 mL, 65.7 mmol), diluted with water, and extracted in EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-(benzyloxy)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid as a gummy liquid (4.1 g) in 83% yield. m/z (M+1), 273; 1H NMR (CDCl3) 300 MHz δ 7.40-7.20 (m, 5H), 4.52 (s, 2H), 2.78-2.70 (m, 1H), 2.58-2.48 (m, 1H), 2.45-2.37 (m, 1H), 2.18-1.50 (m, 9H).

Provenance & Evidence