Formaldehyde → Bis(4,7-dimethyl-2-indenyl)methane

HRID 985780Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.[CH2:12]=O.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1.[C:25]1([CH3:31])[CH:30]=CC=C[CH:26]=1>>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([CH3:12])=[C:16]2[C:15]=1[CH:26]=[C:25]([CH2:31][C:5]1[CH2:4][C:3]3[C:7]([CH:6]=1)=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=3[CH3:1])[CH2:30]2

Participants

Reactant 4

HCID 712Formaldehyde

HCID 1140Toluene

HCID 6101p-Toluenesulfonic acid

HCID 814584,7-dimethyl-1H-indene

Product 1

HCID 11381059Bis(4,7-dimethyl-2-indenyl)methaneYield 44.1%

Conditions

Temperature: 80 °C

Procedure

In a 500 mL flask equipped with magnetic stirring bar were introduced 10 g (0.069 moles) of 4,7-dimethyl-indene, 1.04 g (0.035 moles) of formalin and 2.64 g (0.014 moles) of para-toluenesulphonic acid in 100 ml of toluene; the mixture was heated to 80° C. and was maintained under stirring for 3 hours at 80° C. Then the reaction was quenched with water/NaHCO3; the conversion, measured by gas chromatographic analysis, was 82.4%. 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 5.1 g of bis(4,7-dimethyl-2-indenyl)methane (purity of 90.2% by G.C.; yield=44.1%).

Workup

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

Sources & evidence

ORD record: ord-b5374acbc004471ead25422deb1580ce
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872863B2

Reaction notes

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