Hydrochloric Acid → HCID 23286583, compound

2,3,5,7-Tetrahydro-5,5,8,8-tetramethyl-1H-Benz(f)inden-1-one (14.89 g, 58.08 mmol) and NaBH4 (2.21 g, 58.5 mmol) were stirred in diethylether (200 mL) at 0° C. while EtOH (100 mL) was added slowly. This mixture was allowed to warm slowly to room temperature and then stirred at room temperature overnight. After the reaction period the mixture was poured onto crushed ice and made acidic with HCl. The organic layer was then separated and washed with 1 M HCl (1×100 mL). The volatiles were then removed from the organic layer and the residue refluxed in benzene (300 mL) with p-toluenesulfonic acid (0.12 g) using a Dean-Stark apparatus until no more H2O was evolved. The mixture was then washed with 1 M NaHCO3 (2×100 mL) and the volatiles were removed from the organic layer resulting in the isolation of a yellow oil. Recrystallization from MeOH (0° C.) resulted in the isolation of the desired product as off-white crystals (10.37 g, 74.3 percent yield).

1. additionwas added slowly
2. customAfter the reaction period the mixture
3. additionwas poured
4. customonto crushed ice
5. customThe organic layer was then separated
6. washwashed with 1 M HCl (1×100 mL)
7. customThe volatiles were then removed from the organic layer
8. temperaturethe residue refluxed in benzene (300 mL) with p-toluenesulfonic acid (0.12 g)
9. washThe mixture was then washed with 1 M NaHCO3 (2×100 mL)
10. customthe volatiles were removed from the organic layer
11. customresulting in the isolation of a yellow oil
12. customRecrystallization from MeOH (0° C.)

ORD record

ord-5c00c75bd92a43e29e8e85cf93efb954

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127563