Acetic Acid → bicyclo[3.3.1]nonane-3,7-dione

Participants

Reaction Conditions

Reaction Steps

A suspension of tetramethyl 3,7-dihydroxybicyclo[3.3.1]nona-2,6-diene-2,4,6,8-tetracarboxylate (19.2 g, 50 mmol) in an aqueous solution of 10 M HCl (50 mL), water (50 mL) and glacial acetic acid (100 mL) was heated at 130° C. for 6 h. After cooling at room temperature, the reaction mixture was poured onto crushed ice (200 mL) and extracted with DCM (4×200 mL). The combined organic layers were washed with an aqueous saturated solution of NaHCO3. The organic layer was dried over MgSO4, and concentrated under reduced pressure to give an orange solid. This crude product was dissolved in acetone and the salts which precipitated were filtered. Concentration of the filtrate and washing with Et2O afford the desired diketone (1) as a white solid (6.5 g, 85%).

Provenance & Evidence