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Formaldehyde → HCID 22508181, compound

HRID 985783
Notes
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Reaction equation

HRID 985783 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 5463021-tert-Butyl-1H-indene

Product 1

HCID 22508181HCID 22508181, compoundYield 216.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 79.5%. 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

  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 crystallized
  7. customupon standing at room temperature
  8. customwas further purified
  9. washby washing with MeOH

Sources & evidence

ORD record
ord-8c3191c973994885a8e259692c6db81b
Source dataset
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06872863B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes