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

Temperature

130 °C

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%).

1. temperatureAfter cooling at room temperature
2. additionthe reaction mixture was poured
3. extractionextracted with DCM (4×200 mL)
4. washThe combined organic layers were washed with an aqueous saturated solution of NaHCO3
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated under reduced pressure
7. customto give an orange solid
8. customthe salts which precipitated
9. filtrationwere filtered
10. washConcentration of the filtrate and washing with Et2O

ORD record

ord-d637ae65a3f9496fa4ae19f89f8c6240

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290750B2