Hydrochloric Acid → 9,10-Dihydrophenanthren-2-ol

Then, 2.00 g (11.6 mM) of m-chloroperbenzoic acid was added to a solution of 2.54 g (11.4 mM) of 2-acetyl-9,10-dihydrophenanthrene in 75 ml of dichloromethane at room temperature under stirring to be dissolved therein. To the resultant solution, 1.11 g (11.1 mM) of potassium carbonate was added, followed by heat-refluxing for 2 hours and 10 minutes. After the reaction, the reaction mixture was cooled on an ice bath and poured into 10%-sodium hydrogencarbonate aqueous solution. The resultant organic layer was washed with 5%-sodium hydrogencarbonate aqueous solution, followed by evaporation under reduced pressure to obtain a residue. To the residue, 1.59 g (24.1 mM) of sodium hydride, 25 ml of ethanol and 10 ml of water were added at about 70° C. on a hot water bath, followed by heat-stirring for 0.5 hour. After the reaction, the solvent was distilled-off under reduced pressure from the reaction mixture to obtain a residue. To the residue, 200 ml of water was added and 2.50 ml (28.3 mM) of concentrated hydrochloric acid was further added thereto to precipitate a crystal. The crystal was recovered by filtration and dissolved in ethyl acetate, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) to obtain 1.24 g of 2-hydroxy-9,10-dihydrophenanthrene (Yield: 55.3%).

1. dissolutionto be dissolved
2. temperatureby heat-refluxing for 2 hours and 10 minutes
3. customAfter the reaction
4. temperaturethe reaction mixture was cooled on an ice bath
5. washThe resultant organic layer was washed with 5%-sodium hydrogencarbonate aqueous solution
6. customfollowed by evaporation under reduced pressure
7. customto obtain a residue
8. stirringby heat-stirring for 0.5 hour
9. customAfter the reaction
10. customto obtain a residue
11. customto precipitate a crystal
12. filtrationThe crystal was recovered by filtration
13. dissolutiondissolved in ethyl acetate
14. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent
15. customto obtain a crude product
16. customThe crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)

ORD record

ord-8fed11efb207475ca5c0ee2fa296fab9

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05213709