Acetone → 2,6,6-Trimethylfulvene

HRID 1087370Notes

Reaction equation

HRID 1087370 reaction equation
C[Li].[CH3:3][C:4]1[CH2:8][CH:7]=[CH:6][CH:5]=1.[CH3:9][C:10]([CH3:12])=O>>[CH3:3][C:4]1[CH:8]=[CH:7][C:6](=[C:10]([CH3:12])[CH3:9])[CH:5]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 667751-Methyl-1,3-cyclopentadieneHCID 178418348HCID 178418348, compound

Product 1

HCID 143632822,6,6-TrimethylfulveneYield 85%

Conditions

Temperature
25 °C

Procedure

150 ml of methylcyclopentadiene dimer was fractionally distilled from 100 ml of mineral oil and at 62° C. and collected at 0° C. 500 mmol of methyl lithium (1.4 M; diethylether) were added, dropwise, to a mixture of 500 mmol of freshly distilled methylcyclopentadiene and 137 ml of dry acetone at 0° C. The solution was stirred for 1 hour at 25° C. 8 g (85% yield) of 3,6,6,-trimethylfulvene were recovered from the organic layer by vacuum distillation after an extraction with 100 ml of saturated, aqueous NH4Cl and drying over MgSO4.

Workup

  1. distillation150 ml of methylcyclopentadiene dimer was fractionally distilled from 100 ml of mineral oil and at 62° C.
  2. customcollected at 0° C

Sources & evidence

ORD record
ord-6db9d36166614601b34562788d950d14
Source dataset
uspto-grants-1991_07
Patent number
US05036034

Reaction notes

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