Water → (3,6-Di-tert-butyl-fluorenyl)diphenylmethane

HRID 17252Notes

Reaction equation

HRID 17252 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:11]=3)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.C(C1C=C(C)C(=[C:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)C=1)(C)(C)C.O>C(OCC)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:8]2[CH2:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:11]=3)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 111404373,6-DI-Tert-butylfluoreneHCID 231070913-Tert-butyl-1-methyl-6,6-diphenylfulveneHCID 178418244HCID 178418244, compound

Product 1

HCID 86625022(3,6-Di-tert-butyl-fluorenyl)diphenylmethane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

In a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock thoroughly purged with nitrogen, 3.01 g of 3,6-di-tert-butyl-fluorene (10.8 mmol) was dissolved in 80 ml of dehydrated diethyl ether in a nitrogen atmosphere. To the solution, 7.6 ml of a n-butyl lithium/hexane solution (1.56M: 11.9 mmol) was gradually added dropwise in an ice bath and stirred at room temperature over night. To the reaction solution, 50 ml of a solution prepared by dissolving 4.86 g of 3-tert-butyl-1-methyl-6,6-diphenyl fulvene (16.2 mmol) in 50 ml of dehydrated diethyl ether was added and stirred with refluxing for 13 days. To the reaction mixture, 30 ml of distilled water was gradually added dropwise in an ice bath, and thereafter diethyl ether was added to separate an organic phase. The organic phase was washed with distilled water and saturated brine. The organic phase was dried with anhydrous magnesium sulfate, thereafter the drying agent was filtered off and the solvent was distilled off from the filtrate under reduced pressure to give red solid. The red solid was re-crystallized using ethanol and dried under reduced pressure, and thereby the aimed compound was obtained in an amount of 4.42 g (7.63 mmol) as a pale yellow solid (yield: 71%).

Workup

  1. customIn a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock
  2. additionwas added
  3. stirringstirred
  4. temperaturewith refluxing for 13 days
  5. customto separate an organic phase
  6. washThe organic phase was washed with distilled water and saturated brine
  7. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe solvent was distilled off from the filtrate under reduced pressure
  10. customto give red solid
  11. customThe red solid was re-crystallized
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-06c11135a2de46a6a450d4b90efb84c1
Source dataset
uspto-grants-2010_06
Patent number
US07737239B2

Reaction notes

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