Diethyl Carbonate → Ethyl cyano(3,4-dimethoxyphenyl)acetate
Reaction equation
[Na].[C:2](#[N:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[C:6]([O:7][CH3:8])[CH:5]=1.[C:15](=O)([O:19]CC)[O:16][CH2:17][CH3:18]>>[CH3:8][O:7][C:6]1[CH:5]=[C:4]([CH:3]([C:2]#[N:14])[C:15]([O:16][CH2:17][CH3:18])=[O:19])[CH:13]=[CH:12][C:9]=1[O:10][CH3:11]Participants
4
Procedure
25.7 g (1.1 mol eq.) of sodium in small pieces were added gradually to a solution of 198 g (1.1 mol) of homoveratronitrile in 500 ml of diethyl carbonate in such a manner that the temperature remained at approximately 100°. Thereafter, the reaction mixture was heated to reflux for 1 hour, evaporated under reduced pressure, treated with cooled water, acidified with 70 ml of glacial acetic acid and extracted with ether. The combined organic extracts were dried and evaporated. The residual oil was distilled in a high vacuum, whereby ethyl 3,4-dimethoxyphenylcyanoacetate was obtained, b.p. 170°-172°/70 Pa. HPLC purity >99%.