Acrylonitrile → 4,4-Diphenyl-4-formylbutanenitrile

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Reaction Steps

To a stirred solution of diphenylacetaldehyde (11.0 mL) and acrylonitrile (4.5 mL) in dioxane (125 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10.5 mL). The solution was heated under reflux overnight and then concentrated in vacuo. The residue was purified by a silica gel column eluting with (95:5) hexane/ethyl acetate. The desired product (8.115 g) was obtained a colorless crystals, mp 80-82° C.: MS showed (M+NH4)+ @ 267; 1H-NMR (CDCl3, δ): 2.05-2.15 (m, 2H), 2.65-2.75 (m, 2H). 7.11-7.45 (m, 10 H), 9.80 (s, 1H); Anal. Calcd for C17HI5NO: C, 81.90; H, 6.60; N, 5.61. Found: C, 81.83; H, 6.64; N, 5.65.

Provenance & Evidence