Benzophenone → 6,6'-Diphenylfulvene

HRID 1096301Notes

Reaction equation

HRID 1096301 reaction equation
C[O-].[Na+].[C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:18]1[CH2:22][CH:21]=[CH:20][CH:19]=1>>[C:5]1([C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:21]2[CH:20]=[CH:19][CH:18]=[CH:22]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 3102BenzophenoneHCID 7612CyclopentadieneHCID 10942334Sodium Methoxide

Product 1

HCID 1012366,6'-DiphenylfulveneYield 82%

Procedure

78.0 g (0.24 mol) of sodium methylate solution were initially introduced into a 500 ml four-necked flask at 50° C. and 45.6 g (0.25 mol) of benzophenone were then added. After complete dissolution, 20 g (0.30 mol) of freshly distilled cyclopentadiene were added dropwise in the course of 30 min at 45-50° C. After the end of the addition, stirring was effected for a further 2 h at room temperature, a dark red suspension forming. This was filtered over a G3 frit and the solid was washed four times with 25 ml of ethanol each time. After drying in a vacuum from an oil pump, 47.1 g (0.20 mol; 82% yield) of red 6,6-diphenylfulvene were obtained.

Workup

  1. additionwere added dropwise in the course of 30 min at 45-50° C
  2. additionAfter the end of the addition
  3. customa dark red suspension forming
  4. filtrationThis was filtered over a G3 frit
  5. washthe solid was washed four times with 25 ml of ethanol each time
  6. customAfter drying in a vacuum from an oil pump

Sources & evidence

ORD record
ord-f105d76cd399409c8939b174bfcaf7fb
Source dataset
uspto-grants-2012_03
Patent number
US08138286B2

Reaction notes

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