Hydrochloric Acid → HCID 11379560, compound

HRID 1275867Notes

Reaction equation

HRID 1275867 reaction equation
C=O.[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH3:12][CH2:13][O-].[Na+].Cl>CN(C)C=O>[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:6][C:7]2[C:12]3[C:13](=[CH:11][CH:3]=[CH:4][CH:5]=3)[CH2:9][CH:8]=2)=[CH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7219IndeneHCID 2723922Sodium ethoxide

Product 1

HCID 11379560HCID 11379560, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Formalin (37% solution; 3.5 g, 43.1 mmol) was added to a mixture of indene (10.0 g, 86.2 mmol) and EtONa (2.9 g, 43.1 mmol) in N,N-dimethylformamide (100 mL). The reaction mixture was stirred at room temperature for 12 hours. A solution of HCl (1 M, 50 mL) was added. The mixture was extracted with CH2Cl2 (2×100 mL) and the organic phases combined, washed with a saturated solution of NaCl and then with water, dried over MgSO4, filtered and finally concentrated to yield a viscous brown liquid (89% yield by GC). Vacuum distillation yielded pure bis-(3-indenyl)methane as a yellow viscous oil (b.p. 160-180° C. at 1.2 mmHg, 3.65 g, 35% yield), which can be recrystallized from pentane.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (2×100 mL)
  2. washwashed with a saturated solution of NaCl
  3. dry with materialwith water, dried over MgSO4
  4. filtrationfiltered
  5. concentrationfinally concentrated
  6. customto yield a viscous brown liquid (89% yield by GC)
  7. distillationVacuum distillation

Sources & evidence

ORD record
ord-46593c550682441c8c9eb37cfc0b906c
Source dataset
uspto-grants-2000_12
Patent number
US06162937

Reaction notes

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