Trifluoroacetic acid → 9,9-diphenylfluorene

HRID 2374110Notes

Reaction equation

HRID 2374110 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:12]=[CH:13][CH:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]1([C:7]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:10]3[C:9]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 410659diphenyl-(2-phenylphenyl)methanol2×HCID 516892Sodium Bicarbonate

Product 1

HCID 4135699,9-diphenylfluorene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9,9-diphenylfluorene was prepared from α,α-diphenyl-2-biphenylmethanol by the following method. To a solution of the starting carbinol (0.50 g, 1.49 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (10 mL). After refluxing for 1 hour, the reaction was cautiously neutralized by the addition of aqueous NaHCO3. The mixture was then extracted with Et2O (2×100 mL) that was subsequently washed with additional H2O (100 mL) and brine, dried over MgSO4 and concentrated to white solid (0.47 g, 99% yield).

Workup

  1. temperatureAfter refluxing for 1 hour
  2. extractionThe mixture was then extracted with Et2O (2×100 mL) that
  3. washwas subsequently washed with additional H2O (100 mL) and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-63b00ac7ba8249b69e345181804c9cd4
Source dataset
uspto-grants-2008_12
Patent number
US07462405B2

Reaction notes

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