Formaldehyde → HCID 22508181, compound

HRID 2121099Notes

Reaction equation

[C:1]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].C=O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19](S(O)(=O)=O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]=1[CH2:7][C:6]1[CH2:26][C:16]2[C:21]([C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

In a 500 mL flask equipped with magnetic stirring bar were introduced 12.35 g (0.072 moles) of 1-t-butyl-indene, 1.43 g (0.048 moles) of para-formaldehyde and 2.73 g (0.014 moles) of para-toluenesulphonic acid in 200 ml of toluene; the mixture was heated to 80° C. and was maintained under stirring for 6 hours at 80° C. Then the reaction was quenched with water/NaHCO3; the conversion, measured by gas chromatographic analysis, was 79.15%. The organic layer was separated, washed with water and brought to dryness under reduced pressure. The crude product crystallized upon standing at room temperature, and then was further purified by washing with MeOH, thus isolating 10.8 g bis(3-t-butyl-2-indenyl)methane (purity of 90.9 by G.C.; yield=76.81%).

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 crystallized
customupon standing at room temperature
customwas further purified
washby washing with MeOH

Sources & evidence

ORD record: ord-6bb75edae84c4d09be23b3547864fd95
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693156B1

Reaction notes

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