Fluorenone → 9-Hydroxy-9-methylfluorene

HRID 928865Notes

Reaction equation

HRID 928865 reaction equation
[CH:1]1[C:13]2[C:12](=[O:14])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:15][Mg+].[Br-]>C1COCC1>[CH3:15][C:12]1([OH:14])[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 10241FluorenoneHCID 178418689HCID 178418689, compound

Product 1

HCID 959339-Hydroxy-9-methylfluorene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a glovebox, in a 50 mL round bottom flask, 9H-fluorene-9-one (5.458 g, 30.3 mmol) was dissolved in 20 mL of THF and cooled to 0° C. for 30 minutes. MeMgBr (1.2 eq.) was then slowly added via syringe while stirring. A slurry formed once all of the Grignard was added. The reaction was allowed to stir for 48 hours. The flask was then removed from the glovebox and 4 mL of 2M NaOH were added. The mixture was washed with brine and the organic portion collected and dried over MgSO4, filtered and the volatiles removed under a N2 stream. NMR of the resultant yellow solid showed pure 9-methyl-9H-fluoren-9-ol. Yield is 5.67 g (95 wt %).

Workup

  1. customA slurry formed once all of the Grignard
  2. additionwas added
  3. stirringto stir for 48 hours
  4. customThe flask was then removed from the glovebox and 4 mL of 2M NaOH
  5. additionwere added
  6. washThe mixture was washed with brine
  7. customthe organic portion collected
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthe volatiles removed under a N2 stream

Sources & evidence

ORD record
ord-782cc260a9b4412486fa0e3c01958ca8
Source dataset
uspto-grants-2016_03
Patent number
US09290589B2

Reaction notes

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