Diethyl Ether → p-Benzyloxycinnamaldehyde

Participants

Reaction Steps

Other N-methyl-cinnamylamines can be prepared as follows: To the solution of 5.55 g of di-isopropylamine in 60 ml of diethyl ether, 35 ml of 1.6 molar n-butyl lithium in hexane are added dropwise while stirring at -20° under nitrogen. Thereupon the solution of 6.9 g of N-ethylidenecyclohexylamine in 50 ml of diethyl ether is added dropwise at -20°, followed by the solution of 10.6 g of 4-benzyloxy-benzaldehyde in 50 ml of diethyl ether and 10 ml of tetrahydrofuran at -70°. The mixture is stirred for 1 hour at room temperature, washed with 50 ml of water and stirred with 100 ml of water and 50 ml of acetic acid for 8 hours at room temperature. The ethereal layer is collected, washed with water, N hydrochloric acid, 2N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated, to yield the 4-benzyloxycinnamaldehyde.

Provenance & Evidence