Formaldehyde → HCID 11379560, compound

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).

1. additionwere added dropwise, in 15 minutes
2. customa mildly exothermic reaction
3. additionAt the end of the addition
4. temperaturethe reaction mixture was maintained
5. stirringunder stirring for 20 hours, at room temperature
6. customThe reaction was quenched
7. additionby pouring the mixture on ice and NH4Cl
8. extractionThe organic product was extracted with Et2O
9. washthe water layer was washed with Et2O
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationfinally concentrated
13. customthus obtaining an orange-brown oil
14. concentrationwas further concentrated

ORD record

ord-23554cae985446c89035678571021c1e

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06162937