Hydrochloric Acid → HCID 22117991, compound

HRID 1275869Notes

Reaction equation

HRID 1275869 reaction equation
C=O.[CH3:3][C:4]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]2[C:5]=1[CH:6]=[CH:7][CH2:8]2.[CH3:14][CH2:15][O-].[Na+].Cl>CS(C)=O>[CH3:3][C:4]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]2[C:5]=1[C:6]([CH2:10][C:9]1[C:5]3[C:6](=[C:15]([CH3:14])[CH:11]=[CH:12][C:4]=3[CH3:3])[CH2:7][CH:8]=1)=[CH:7][CH2:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 814584,7-dimethyl-1H-indeneHCID 2723922Sodium ethoxide

Product 1

HCID 22117991HCID 22117991, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Formalin (37% aq. solution, 0.28 g, 3.47 mmol) was added to a mixture of 4,7-dimethylindene (1.0 g, 6.94 mmol) and EtONa (0.15 g, 2.20 mmol) in dimethylsulphoxide (10 mL) at 25° C. After stirring at room temperature for 12 hours, the reaction mixture was heated at 80° C. for further 4 hours and then cooled to room temperature. A solution of HCl (1 M, 10 mL) was added. The mixture was extracted with CH2Cl2 (2×50 mL); the organic phases were combined, washed with a saturated solution of NaCl and then with water, dried over anhydrous MgSO4, filtered and finally concentrated to yield a brown solid (GC analysis shows 75% conversion). After washing with MeOH, bis(4,7-dimethyl-3-indenyl)methane was isolated as a yellow solid (0.52 g; yield 50%).

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for further 4 hours
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with CH2Cl2 (2×50 mL)
  4. washwashed with a saturated solution of NaCl
  5. dry with materialwith water, dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationfinally concentrated
  8. customto yield a brown solid (GC analysis shows 75% conversion)
  9. washAfter washing with MeOH

Sources & evidence

ORD record
ord-d72cb75e9a3d44dc99b405ccd466d724
Source dataset
uspto-grants-2000_12
Patent number
US06162937

Reaction notes

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