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

HRID 2121097Notes

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

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%). The results of the 1H-NMR analysis correspond to the ones reported above.

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-91c868a0e18344a8bb4846bec77f9ed3
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693156B1

Reaction notes

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