4-(Dimethylamino)Benzaldehyde → HCID 54256011, compound

Participants

Reaction Steps

A solution of 1.84 g (10 mmoles) of 2,3,5,6,7,8-hexahydro-1H-benz[f]inden-1-one (12), 1.49 g (10 mmoles) of p-dimethylaminobenzaldehyde, and 0.44 g of sodium hydroxide in 25 ml ethanol was stirred under nitrogen at 50° to 60° for 19 hr. The reaction mixture was cooled in an ice bath and the precipitated solid 2-[4-(dimethylamino)phenyl)-methylene]-2,3,5,6,7,8-hexahydro-1H-benz[f]inden-1-one was collected by filtration and washed with cold ethanol. Yield: 2.5 g (79%); m.p. 161° to 163°. λmax (EtOH): 274 nm (ε=16,700); 422 nm (36,500). Calcd for C22H23NO: C, 83.24; H, 7.30; N, 4.41. Found: C, 83.01; H, 7.73; N, 4.34.

Provenance & Evidence