Formaldehyde → Bis(3-methyl-2-indenyl)methane

HRID 985781Notes

Reaction equation

HRID 985781 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]=1.C=O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]=1[CH2:1][C:2]1[CH2:23][C:13]2[C:18]([C:3]=1[CH3:4])=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 130253-Methylindene

Product 1

HCID 22508196Bis(3-methyl-2-indenyl)methaneYield 247.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a 500 mL flask equipped with magnetic stirring bar were introduced 14.8 g (0.114 moles) of 3-methyl-indene, 2.3 g (0.077 moles) of para-formaldehyde and 4.37 g (0.023 moles) of para-toluenesulphonic acid in 200 ml of toluene; the mixture was heated to 80° C. and was maintained under stirring for 1 hour at 80° C. Then the reaction was quenched with water/NaHCO3; the conversion, measured by gas chromatographic analysis, was 85.9%. The organic layer was separated, washed with water and brought to dryness under reduced pressure. The crude product was crystallized upon standing at room temperature, and then was further purified by washing with pentane or MeOH, thus isolating 15.5 g of bis(3-methyl-2-indenyl)methane (purity of 89.8% by G.C.; yield=89.8%).

Workup

  1. customIn a 500 mL flask equipped with magnetic stirring bar
  2. temperaturewas maintained
  3. customThen the reaction was quenched with water/NaHCO3
  4. customThe organic layer was separated
  5. washwashed with water
  6. customThe crude product was crystallized
  7. customupon standing at room temperature
  8. customwas further purified
  9. washby washing with pentane or MeOH

Sources & evidence

ORD record
ord-13eebd2149c047918408e567463162eb
Source dataset
uspto-grants-2005_03
Patent number
US06872863B2

Reaction notes

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