Hydrochloric Acid → HCID 15824187, compound

HRID 1387759Notes

Reaction equation

HRID 1387759 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=O)C>[CH:3]1([CH2:9][CH:8]2[C:12]3[C:13](=[CH:11][CH:3]=[CH:4][CH:5]=3)[CH:6]=[CH:7]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7219IndeneHCID 2723922Sodium ethoxide

Product 1

HCID 15824187HCID 15824187, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.5 g of formalin (37% solution, 43.1 mmol) was added to a mixture of 10.0 g of indene (86.2 mmol) and 2.9 g of EtONa (43.1 mmol) in 100 mL of DMF. 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 bis(1-indenyl)methane as a viscous brown liquid (89% yield by GC). Vacuum distillation yielded the pure product 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

Sources & evidence

ORD record
ord-6f1ff9b9ee0f4734a85d3272ef880fa7
Source dataset
uspto-grants-2001_07
Patent number
US06268518B1

Reaction notes

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