Methanol → 2-(Methyloxy)-4-(2-oxoethyl)benzonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH:12]=C)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].CSC.C[OH:18]>>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH:12]=[O:18])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]Participants
4
Procedure
To a 25 mL flask containing a stir bar was added compound 2-(methyloxy)-4-prop-2-en-1-ylbenzonitrile (0.15 g, 0.87 mmol) and MeOH (8 mL). The flask was placed in a cold bath of −78° C. Ozone was bubbled through the flask for about 10 min. followed by addition of dimethyl sulfide (1.5 mL, 24 mmol). The flask was taken out of the cold bath and stirred at room temperature for 1 h; LC indicated completion of the reaction. The reaction mixture was concentrated to dryness to give 2-(methyloxy)-4-(2-oxoethyl)benzonitrile. LC-MS (IE, m/z): 176 [M+1]+.