Diethyl Ether → 9-(3-Methylphenyl)-9H-fluoren-9-ol

HRID 1275735Notes

Reaction equation

HRID 1275735 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([Mg]Cl)[CH:2]=1.[CH:10]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1.C(OCC)C>O1CCCC1>[CH3:9][C:1]1[CH:2]=[C:3]([C:21]2([OH:23])[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[C:22]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10241FluorenoneHCID 178425419HCID 178425419, compound

Product 1

HCID 52421279-(3-Methylphenyl)-9H-fluoren-9-olYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1.0 M solution of m-tolylmagnesium chloride in tetrahydrofuran (10 mL, 10 mmol) (Aldrich) was added dropwise to a solution of 9-fluorenone (1.8 g, 10 mmol) (Aldrich) in anhydrous tetrahydrofuran (5 mL) with stirring under argon at 0° C. The mixture was stirred at room temperature for 1 h, anhydrous diethyl ether (20 mL) was added and the formed precipitate was filtered and dissolved in chloroform (50 mL). The chloroform solution was washed with a saturated solution of ammonium chloride (10 mL), brine (10 mL), dried (MgSO4), the solvent evaporated and the residue recrystallized from diethyl ether/hexane to give the title compound as a white solid (2.42 g, 89%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. filtrationthe formed precipitate was filtered
  3. dissolutiondissolved in chloroform (50 mL)
  4. washThe chloroform solution was washed with a saturated solution of ammonium chloride (10 mL), brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. customthe residue recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-fc539dee00be44e6baf8d07c16cc9f5b
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

Loading…