Hydrochloric Acid → 9a-BUTYL-7-HYDROXY-4-(4-HYDROXYPHENYL)-1,2,9,9a-TETRAHYDRO-3H-FLUOREN-3-ONE

Temperature

0 °C

An ice-cold solution of 9a-butyl-4-(4-hydroxy-phenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29 mg, 0.08 mmol) in anhydrous CH2Cl2 (1 mL) was added to AlCl3 (96 mg, 0.72 mmol) contained in an ice cooled flask. The mixture was stirred at 0° C. under a nitrogen atmosphere and treated with 2-propanethiol (0.056 mL, 0.6 mmol). The resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 3.25 hours, then treated with ice (approx. 2 mL), 2N HCl (2 mL) and EtOAc (4 mL) and stirred for 15 minutes at room temperature. The EtOAc layer was separated, washed with 1N HCl and brine, dried over MgSO4, filtered, and evaporated under vacuum to give a yellow gum. This material was triturated with benzene to give, after filtration and drying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid.

1. customcontained in an ice cooled flask
2. stirringThe resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 3.25 hours
3. stirringstirred for 15 minutes at room temperature
4. customThe EtOAc layer was separated
5. washwashed with 1N HCl and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated under vacuum
9. customto give a yellow gum
10. customThis material was triturated with benzene
11. customto give
12. filtrationafter filtration
13. dry with materialdrying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid

ORD record

ord-97264f6f2909414bad48b9659123da7c

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07087599B2