Formaldehyde → HCID 11379560, compound

Participants

Reaction Steps

1.05 g of EtONa (15.4 mmol) dissolved in 200 mL of DMF and 10.0 ml of indene (90%, 77.5 mmol) were introduced, at room temperature, in this order in a three-neck, 500 mL flask with stirring bar. 3.15 mL of aqueous formalin (37% solution, 38.8 mmol) dissolved in 10 mL of DMF were added dropwise, in 15 minutes: a mildly exothermic reaction was observed and the solution turned dark brown, with shades of violet. At the end of the addition, the reaction mixture was maintained under stirring for 20 hours, at room temperature. The reaction was quenched by pouring the mixture on ice and NH4Cl. The organic product was extracted with Et2O and the water layer was washed with Et2O; the organic layers were combined, dried over MgSO4, filtered and finally concentrated, thus obtaining an orange-brown oil. Said oil was further concentrated to eliminate the remaining indene, thus yielding 9.56 g of bis-(3-indenyl)methane, as an orange-brown oil (53.2% yield by GC).

Provenance & Evidence